Being "owed" things...

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I notice I have a massive problem with this. Sometimes I sell something to someone, they might not have money on them and I just tell them to give it to me some other time like it does not matter that much.

But even with small amounts of money it matters to me a lot, this irritation often does not surface till much much later. Leaves a wake of mess, and unfinished mental project that needs that money for closure. But because it has been left so long, sometimes years, it is just to strange to storm over to acquaintances that I might not have seen in two years and demand $50 of them.
The things I sell are low value items which are extremely difficult to make a profit out of, I work very hard to hunt down deals and go to great lengths to source things for saving pennies and tend to sell stuff to people I know at cost. So I expect the courtesy of actually receiving that money but I suck at following it up. And I really cannot let it go, it really rustles my jimmies.

The problem is intertwined with a social issue I have, where I do not "maintain" friendships through regular social gatherings, I often (not intentionally) ignore "friends" or would-be friends for months or years because none of the said social gatherings interest me. If I happen to see them at something I am at, I expect the same closeness/dialogue to continue like we had seen each other a few days ago, but it does not always seem to work that way.

Without speaking to the third paragraph, I've known many individuals who had issues with "asking people for money". Since most of the transactions that we have in our daily life are "cash on the barrel" or "plastic", many of us don't have experience with the "receivables" side of transactions.

The best advice I can give you is that it doesn't appear to be a hard-wired trait, more of an acquired skill in how to collect accounts receivable.

In your mind you cannot treat it as a loan. Treat it as a gift. I used to have problems with that too. I just could not believe that a person would not (a) pay you back and (b) not have it appear to bother them. If you cannot afford to gift it, then don't give it. I give to a lot less people too.

I have a massive issue with not wanting to lend things to people because I am too worried they will do something to ruin it or not give it back. Even something of little value I just don't want to lend. I would never sell something to someone without them being able to pay me there and then. I too would have years of resentment if someone did something like that to me so I don't ever, under any circumstances allow the situation to arise in the first place.

I don't think it's helpful to tell OP to treat the items like a gift as that is missing the point. It's the fairness aspect of it, OP wants rightful recompense for what he gives, he never intended it like a gift. So the only solution is to not give over the item until the person has the money.

The thing is OP, it clearly does matter to you, so you are telling people "it doesn't matter, give it later" and people (particularly NTs) will take this to mean that you aren't even bothered about getting something for it. Just tell them in future, "I will hold it for you until (date) to give you a chance to get the money". If they don't come up with the money, then they were never that bothered or cannot come up with it. If they question why you are doing that be honest, tell them you have had way too many experiences where people "forget" to pay so you have made it a blanket rule as you have been out of pocket so much.

As above, 'Don't ask for credit as a refusal often offends'.

It's not like you are losing profit or repeat custom.

At this point in time I feel it may be best to wipe the slate clean and start again. Otherwise you may end up with a persistent list of debtors which will continue to make you bitter and affect your life.

It was my awkward way of saying that I do not lend anything, I give "gifts" infrequently because that is the best way for me to deal with the persistent stress of seeing that person with passing/no acknowledgement of his/her debt. It is more healthy for me to deal with it that way than to agonize over person that has a debt with me.

I'm a bit harder than you I think! The only time I gift is at birthdays and Christmas. (except for buying treats for my children). Even if I gifted in the way you describe I would be feeling resentful that I'd felt obliged to do it and not wanted to.

I don't feel that stress inside me is worth it!