Honestly, if his budget is ignoring property taxes, etc (which because he's looking at his home as part of his property investment it seems, isn't really in the $500), with $50 for food, $500 isn't unreasonable. I have about a $30-50 a month electrical bill, and with some HD insurance, it's pretty reasonable. I kind of don't care if he's a troll or not, as I find the thought/problem games interesting the first few times, and it's a particular formulation that I haven't played before. I'm not going to date him, so unless/until continuity is broken, I don't care if he's real.
That said, more ideas for the particular situation:
You enjoy shopping - very cool. Look online for Meetup or something similar, and look at planning a "frugal dinner" or something similar - everyone needs to bring up to $20 worth of food to contribute (make them bring receipts) and as a whole plan and make a multi-course dinner. People get competitive over getting good deals (and let me tell you, you'll probably win, which makes you look good), there is a lot of creativity involved in planning the menu and cooking it, it's a great excuse for interaction, and at least a couple of people will bring good cheap drinks to contribute, so you're not wasting money on booze, and they don't have to spend the time and learning curve to do the sort of creative/coupon shopping you manage to do. Heck - you have multiple rental buildings, so you must have at least a couple of vacant units - be the host! if they are materialistic, at least they will be impressed with your building, if not your clothes, and playing host puts you on a pedestal as well. much easier to find someone when they are trying to catch you.
find some local artists, and set up guerrilla galleries in vacant units you have - one weekend only shows in vacant units, word of mouth only. meet interesting, creative people, heavily biased to gay men, again play host, no cash cost to you, exclusive event where it costs you no cash but makes you look/be generous with something that has limited marginal cost to you, and you might enjoy the art! heck, some of the artists might barter some interesting art work for a limited showing sometime - good way to acquire things that you like. Also, artists are very used to living broke, and can appreciate frugality, but are likely to be able to help you be frugal and "hip" opr fashionable. If you are looking to attract gay men cheaply, you need to be put together, throwing money at it helps, but doing it cheaply and fashionably is better in some circles.
take up online video games - major time sink, some socialization at keyboard remove. probably not going to get you a date though.
write a book! you've managed to accomplish something that a lot of people would kill for. some people might pay for you to tell them your story, whether to copy it or to inspire them, or someone already on that path to convince them that they are not insane. Someone asks what you do, you can tell them you're an author and a arts sponsor. (via having the gallery stuff) that ought to get some attention.
As I said - I don't care it it's a troll, because games are fun. If the OP isn't a troll, hopefully we can help him. Anyone else have good ideas? Rules seem to be: aversion to spending money, semi-social personality with some issues about being judged on a materialistic basis, gay single male, 30, time to spend, reasonably educated, probably enjoys problem solving (coupon shopping "game" success level), and reasonably intelligent.
