In the spirit of the sub, I'm writing this to get some new perspectives on a small roommate argument that's been consuming my attention. Partially also to sort it in my own head. Here goes: 

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Recently, a low value item (\~$5) was traded between myself and my roommate, or rather, I gave it to him with the expectation he would pay me back (this was clear to both me and my roommate). 

Some days pass, maybe 3 or 4, during which I semi-jokingly remind them at least once that he still owes me for the item, and that he can just Venmo me $5. I felt what I perceived as some pushback to this, joking that he just wouldn't pay me back, or I should wait until he gets cash. This bothered me slightly; I felt it wasn't really his place to decide the terms on which I get paid or when I get paid, but at the time it wasn't a big deal. 

Sometime soon after, maybe that next weekend, my roommate leaves for a couple days. I take the opportunity to go into his room and take the item back. 

I'm not sure how this will be perceived here, but I can honestly say that at the time I didn't see it to be a big deal; the reaction I expected was along the lines of, "Oh ha ha, very funny, I'll pay you back now just give me the item back", and it would be over. I guess I thought this because that's how I figured I would react.  

Instead, I very clearly stepped on his toes, and when he found out the item was gone he barged into my room pretty pissed, and demanded the item back. I gave it to him, and received Venmo payment minutes before.

After this point, it kind of died between myself and my roommate. We didn't discuss it, but he was acting cold to me afterwards, the only time I can remember in our friendship that things were this uncomfortable between us. It only came up again maybe 3 weeks later when I was drunk one night and we talked about it. 

The talk started with them asking if I'd realized he was acting distant from me recently, and if I realized that I'd done something to them to make them act this way. This was a few weeks later, so I had to stop a try to recall for a moment what I'd done, but remembered this incident pretty quickly and brought it up. 

I'll try and express their side of the argument as truthfully as possible. It was a long talk, but essentially he said that he thought it was petty of me to take the item back when it was such low value, that friends don't do that because they respect and trust their friends to pay them back, that the $5 obviously wasn't going to break the bank for me and it wasn't worth invading their privacy to send that message. "You're not a mob thug, you don't have to 'send a message' to me to pay you back, we're friends". 

I expressed in return that the price of the item didn't matter, it was based more on principle that I don't like having debts between friends, and I try to pay my friends back as soon as possible to erase the debts because I respect the friendship. I also brought up that, given how little time it actually takes to Venmo someone money, there isn't really an excuse to not have paid someone back asap and that I refused to believe he didn't have 2 minutes of free time in the week after the exchange. I also expressed that going into his room while they were gone was clearly a mistake and apologized for that, saying that if I'd known how it would affect them and the friendship, I would not have done it.

This is way longer than I thought it'd be now, so to wrap it up, I feel a little bit like I tried compromising, and pushing for us both to accept that I should have respected the friendship more and given him more time to pay me back, while by the same token he should have made it a point to pay me back a bit earlier, but we didn't know how each other would react; I thought paying back friends promptly was the respectful thing to do, he thought giving friends time to pay each other back shows respect for the friendship.  He seemed to view this compromise as a loss, saying that If we both do that he is just conceding to my demands by paying me back earlier. I also have a problem with how long this grudge has been held; it's quite a bit after the initial incident now, and talking about it only seemed to make the friendship even more uncomfortable. 

So tell me what you guys think: Does the price of the item matter? I know I misjudged how invading his privacy would make him feel and I've apologized, that's not really the point of contention, but am I wrong for thinking this is not a grudge-worthy incident? Should I have final say on how and when I get paid?

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TL;DR I "stole" back my own property from my roommate after he took longer than I thought was reasonable to pay me back. I didn't see it as a big deal, but it has affected the friendship disproportionately (in my opinion, of course), and talking about it has only made it worse. Do friends give each other time to resolve debts, or do friends resolve debts immediately? Do friends hold grudges over this type of thing? Does the price of the item matter? Am I the asshole?