Is it a sin to desire to not have to repent? If so, was Jesus a sinner?

Behold, I am he that gave the law, and I am he who covenanted with my people Israel; therefore, the law in me is fulfilled, for I have come to fulfil the law; therefore it hath an end. (3 Nephi 15:5)

The New Testament purposefully does not contain such language as this. The Law is absolutely still in effect because God himself declares it eternal.

Yes

You like self-identifying as a sinner?

to elaborate, the inability to admit one's sins and acknowledge oneself as a sinner, is a sign of pride. And pride is most definitely evil, as it implies you're putting yourself above God.

Then you think God is proud.

it doesn't matter whether we like it or not, the point is we need to acknowledge it in order to keep ourselves humble.

Don’t get me wrong, I’m constantly scanning my heart for reasons to reckon myself a sinner, and constantly giving others the benefit of the doubt at the expense of myself. Sin per se is something I’m hyper-concerned with.

God isn't a human. He is the eternal standard. It is logically impossible for him to put himself above himself. But if you or I put ourselves above him, then we're just deluding ourselves into thinking we're the eternal standard for all humanity, and that is pride.

In other words, I live with the assumption in my heart that I’m a sinner, and would even call myself circumcised of heart, and it’s precisely because of this that the thought that I have anything to repent over confuses me.

For the sake of clarity I don’t think it’s possible for anyone to put anything above the status of “God.” What we are talking about is equation with God at worst.

That suggests you have an incomplete view of salvation. Salvation isn't a once-and-done deal that magically absolves you of all future sins, it is an ongoing process. So long as you remain alive, you have to maintain your efforts to reach salvation, because real salvation doesn't happen until the resurrection.

see:
youtu.be/IjHGtCHyBrU
youtu.be/FlJvDz3ZtTw

Ok. So what you are telling me is that I’m a crypto-Christian who doesn’t go around bragging to others that he’s a sinner? I’m ok with that.

If someone goes around publicly stating that they're a sinner for the sake of showing off, then they're doing it wrong. But if they can't publicly declare that they are sinners either, then they're also doing it wrong, because both behaviors are just 2 sides of the same coin. The point is to genuinely engage in humility and not try to dodge it. Intentionally evading the personal responsibilities Christ asked from us, is to effectively deny him. We aren't expected to follow through on them perfectly, but using our gift of free will to selectively absolve ourselves of responsibilities doesn't exactly bode well.

I argue this with Muslims all the time. What does Christ want from us, really, other than Matthew 22:35–40?

I would flip that question around, and ask you what you want from Christ, realy.? You're clearly looking for a very specific kind of answer. Why is that? Surely we can agree that Matthew 22:35–40 wasn't the entirety of Jesus' message, for if it was, he wouldn't have needed the entire NT to tell it. So what was it about those verses that drew you as opposed to all the others?

Because he says the entire law and prophets hang on those two commands, and because kindness and love of creation and the creator makes for a robustly good life philosophy that is easy to share with friends and loved ones without the baggage of orthodox Catholicism.

…especially compared to a Christianity with harsh Pauline emphasis on sin, a concept which everyone with a conscience living in a Christian society implicitly already knows (at least in terms of feeling that they can always do more to help their fellow man)

…and living in a constant state of guilt for failing to always be doing more. Very common in Canadian culture at least.

I guess my observation is that Christians love to act like Christianity is rocket science. It’s not.

tl;dr
Yes
No

I don’t understand what point you are making. Can you put it less cryptically?

It's not a cryptic message for people that have been on imageboards for a while.
Let me rewrite something more detailed anyways.

Form what I understand:
This implies that if the human desires in Jesus Christ made him a sinner. Not so, because its never impossible to avoid sinning.
Have concrete examples:
Sinful
Sinful
Not sinful.

Okay I screwed up the grammar here.
Sorry but its kinda late at night, instead of fixing the mistakes I'll have to go to sleep. I hope my message makes sense either way.

Now we're getting somewhere. This I can understand, because I was born to Catholic parents, which in turn made me a staunch atheist for most of my life, partially due to all the shenanigans surrounding the church. However, as you may have noticed if you checked out any of the prior resources I've cited, they've all been Eastern Orthodox.

My own journey out of atheism is a long story, but as to why I ended up at Eastern Orthodox, I can easily attribute it to that idea of it having significantly less "baggage", with a larger emphasis on how to live out Jesus' philosophy, in a way that's much easier to share than telling everyone they're damned to the lake of fire. There's no way I can summarize the details of all that here, so check out:
youtu.be/62CBupYhHrw
youtu.be/MD6SfHI6-HM
youtu.be/-_qyafJghA0
youtube.com/playlist?list=PLbDsxw-e0m3mIkapUEZ_-5BEOr19F4t73

Additionally, it's important we don't accidentally reduce Jesus to some mere 'ultimate life coach' type figure, just because of the baggage that may come along with following him, because that does actually defeat the purpose:
reformed.org/books/chr_and_lib/
ccel.org/ccel/chesterton/orthodoxy.html

In other words, the point in following a long established church tradition isn't to chain you down, but to learn from 2,000 years of experience of what has actually worked for people. Despite their flaws, they're still more reliable than any one person's fallible intuition. So to go off on your own and start Protestant denomination #5282476 is just needlessly reinventing the wheel, and opens you up to all kinds of ways of unintentionally going wrong. Christianity might not be rocket science, but it's not a loose "do what you feel like" endeavor either.

yes, these are very Western phenomena, stemming from the Roman Catholic church's over-emphasis on the teachings of St. Augustine, which in turn also influenced Protestantism. Eastern Orthodox is very different. Not to say we don't have any Pharisees of our own, but it's certainly a lot less pronounced.

Eastern Orthodoxy is cool! I am interested in it, especially as a Bulgarian. ;)

However, I am under no illusion that I would be able to recruit all my Canadian loved ones to Orthodoxy, people whose salvation I take for granted because of my faith in God, all of whom love God and have plenty of Augustinian guilt (a prerequisite for friendship with me — so much so that I can hardly befriend a cultural Buddhist). As much as I am interested in Orthodoxy (and all things Christian), I am not going to dive into it and leave them behind in the process.

For the record, the bulk of my formal Christian learning has come through correspondence with my high school’s Anglican minister, a Harvard divinity grad whose faith and erudition are inspiring. He provides me with a constant stream of interesting authors to read, similar to you, but nothing he has ever said has contradicted my interpretation of Jesus’ words which say that the entirety of true religion is “love God and also others as you love yourself.”

Not that I want to press conversion or anything, but it is worth keeping in mind that Jesus himself said
Now obviously he didn't suggest we should disregard our families, but rather that they are ultimately in charge of their own salvations as we are of ours. And often times the best we can do is lead by example and pray. So you should focus on your own relationship with God first and foremost, and take in as much of the teachings of the early church fathers as you can, so you can start incorporating their wisdom into your everyday life, and hopefully inspire your family to learn their ways as well. No need to reject your family's Catholicism, nor your church's entire body of teachings for that, just show them an authentic alternative way of living out the love of God in yourself, and hopefully they'll recognize 'the way' without you having to preach too much. Doing this masterfully may require much study, prayer, and patience on your part of course.

Well it is certainly a very good elevator pitch rendition of the faith, the tricky part however, is that we humans are also very prone to loving ourselves a little too much unfortunately. And that's where all the other teachings come in to help keep us from falling into that trap. Hence it's risky to throw away too many of the church's established teachings and traditions, because they've basically been built around helping us prevent that.

Good point. That’s not when I meant when I talked about leaving them behind. Of course I love God more than any family member or friend.

What I meant was

Loving yourself isn’t un-Christian per se. The command is to love others as you love yourself, so as long as you are obedient to Christ, the more you love yourself, the more you will love others. Conversely, if you only love yourself very little, then you will not be loving others very much. (Especially if despite your lack of self-love you somehow manage to love God very much — this is presumably is the Christian misanthrope archetype, which truth be told, is a little bit how I imagine Orthodoxy)

I would add that Christ obviously loves himself. The love of God, and the love of God of God, is precisely why Christ is so generous in love. Love loving itself loves all things. So I genuinely don’t think there is a valid basis to say that “we humans are also very prone to loving ourselves a little too much unfortunately.”

I would be interested to hear if Orthodoxy teaches something different to what I’m saying here.

Well, it's a bit of a semantic issue, because "love yourself" can in fact also loosely describe literal Satanist doctrine, and that is not a coincidence.

The question then is, what do we mean by "love"? Because the entire belief system hinges on interpreting that correctly, and it is something that requires nuanced explanation (like how St. Maximus the Confessor laid it out in his chapters on love), because otherwise it is very prone to misinterpretation. Many people in the modern secular West literally view "loving themselves" as something that entitles them to play God for example, and that is diametrically opposed to what the gospel was about. This is because it is very easy to conflate pride with self-love. You may be aware of this distinction yourself, but without emphasizing it to others, it is very easy to lead them astray, because people will always prefer to hear what they want to hear. Just look at the entire "new age spirituality" movement in the West to see that in action. There are very many "hippies"/"witches"/"gurus"/etc that claim to love themselves and everyone around them very much, but that doesn't make them Christians.

Well, it certainly teaches love, but it also teaches that we each need to pick up our cross, and endure carrying it through the rocky uphill path of life. The cross is heavy and the gate is narrow, but when we accept the Truth, God can help guide us up the ladder of divine ascent. In other words, if following Jesus appears too easy, we're probably missing something.

In the two great commandments, love of God comes first, and I think it would be difficult to love God and be a Satanist. But I will be even stronger and say that if witches or Buddhists claim to love anything, they are lying. For how could anyone love anything if they didn’t love God first? The two great commandments even conflate love of God with love of “the other” by saying “the second great commandments isnloke unto the first.”

The words of non-Christians simply be trusted, so you shouldn’t take what they say as reason to mistrust what a Christian is saying. I do trust myself that I love God. I know that when I say I love myself and my loved ones, that is not false love which wants anything in return, but is love which is by the grace of God.

Simply can’t be trusted, it should say

I will add that if someone wants something in return for my friendship or my love, then I simply don’t love that person. Therefore, I know also that the love shown to me by friends and loved ones is also by the grace of God, and that they too love God.

Do you see a flaw in my logic? Is it conceivable that me and the people in my life are all accidentally or secretly worshipping Satan? If my logic isn’t airtight I want to know.

Ultimately we can never truly know what's inside another human's heart, so it is always possible that some around you may accidentally dabble in heresy, but you can only help reduce the likelihood of that by being nuanced about the message of the gospel. This is why Catholics and Orthodox have catechumen sacraments after all. So I wouldn't be too concerned about people accidentally worshipping satan for example, but rather I'd focus on learning to identify pride, being careful to avoid pride, and helping others when they show signs of pride as well. Because it is pride that is the source of many other sins/heresies, and you can never underestimate the impact living in a prideful secular culture has on many well-intentioned Christians. Just the other day, I had an educated and confirmed 'cradle' catholic telling me that it is impossible for anyone to prove God, or for any religion to have 'the Truth', and then went on to question the resurrection and virgin birth, all while still affirming that he was a devout Catholic!

But anyways, it sounds like you have a good head on your shoulders with a genuine heart, so all I can suggest is to continue your studies about the faith, and learn directly from the wisdom of the saints and church fathers if you do nut trust current church authorities themselves. Nuanced understandings and the gift of discernment (see vid related) only come with time.