There may be as many answers to this is there are Buddhists. To me, it seems the major thing is that one is mindful of gift giving such that the gift is clearly for the benefit of the recipient and not the giver. The "in season" would seem to speak to the appropriateness of a gift. Something given "out of season" could either be wildly extravagant or something one had laying around for a long time & decided that giving it as a gift would be a good way to "get rid" of it.
As I've said elsewhere, I'm not too keen on the idea of being picky about what someone is going to do with a gift of money. A gift given "with conviction" isn't one with strings attached. If someone is begging on the street corner, there may be a perfectly good reason for it. You don't want to give $100 to a street corner beggar or to an irresponsible child. But giving enough to get a meal is fine, in my book. A long time ago, I was sitting at a bus stop and a bedraggled lady in her mid-twenties came and asked for $.50 for a hamburger (the stop was in front of a McDonalds and it was a LONG time ago). Having no extra change, I gave her a dollar. A man next to me said "You just helped her buy beer or drugs". I just said, "Maybe." As we both watched, she went into McDonald's and come out with a burger & fries, sat on the curve and ate it greedily. I told the man, "You never know". And that's it, you don't know. I always give to street corner beggars if I have the money. If they "live better than I do and don't work", well, that's better than if I didn't give and that person went without food for days.