You do have to be careful about developing generosity - helping others when you later become the person needing help. When we went to India, we were told by the Indian Embassy, "Don't give to beggars. The government has everything solved", on the airplane going over. And on a Indian airline, they handed us pamphlets, telling us how to "do things right" in India and not to give to beggars, they have everything solved, the government is taking care of the whole world.
So, okay, we were not supposed to give to the beggars in India, that's pretty clear, the government doesn't want it. We get to India, to New Delhi, and we stayed in Old Delhi which is quite a bit different to New Delhi. In Old Delhi there were beggars everywhere. There were sometimes 50 beggars lined up on the street. They were just everywhere. They come up to you, they want money, they want this, they want that, everywhere. The first day Rosemary and I reacted by thinking, "No, no, we're not supposed to give to the beggars, not supposed to give to the beggars." Second day I think we tried the same thing, by the third day it wasn't quite working because it was pretty clear that the government was not doing anything for these people.
So we cashed a certain amount of money into one Rupee notes, which back in those day was maybe one Baht each. I had this big pocket full of one Rupee notes. Beggars came up, out came one note, out came one note, when fifty were finished at the end of that day, that was it, we had a limit, because if we started giving more than that, we were going to end up being broke ourselves. So yes, we want to be generous to these people, but yes there is a limit, otherwise we suffer in the end. But not giving anything at all, we couldn't do that, we did want to give.
Now, in relationship to giving away money but without any income. Well, you might have a little to spare, but how much is that little, and be careful because if you don't have any income at that time, you have to take care of yourself and consider yourself as another human being who needs some help. That's just using common sense, having compassion for yourself.
The first part of the question though, giving things that you like to others and then regretting it later. This is more or less an unhealthy attitude, so if you really want to keep that item, don't give it away, because regretting it later just brings more self-hatred. If you can, if you really think this is a wonderful item to give to others, and you really would like to give it but you don't want to give yours, okay, buy a second one that looks the same and give that to them instead. Even if it's not exactly the same but similar. If you really feel it's a great gift to give, but you can't give your own, okay, don't. But regretting it afterwards is more of a problem than going and buying some more and giving those instead. The regret can turn into all sorts of self-hatred, and then you're going to be hesitant in giving away things in the future, your going to spoil it all, you're going to get into doubt, you're going to have a super hindrance attack. It's not worth it.
Somebody else would say, go ahead, give away the most important things you have, that will prove that you can "really do it", but we're not into that here. We're into giving as much as you can possibly give. Give something every day if you can, but if something is so important to you that you regret giving it later, then save that one for another time, give something else instead.