The successful professional GMs I know about fall into three categories:
1) Game designers/writers whose fan base is willing to pay for the experience of playing a game with someone whose work they admire. Examples are Dave Arneson's charity auction games or Ken Hite's walking tour/Call of Cthulu game I organized through Otherworld Excursions.
2) GMs who run games for kids. Having a background in education may be useful - that's the route that led Becky Thomas to start the
Roleplay Workshop.
3) GMs who happened to be in the right place at the right time to be hired by a group of well-to-do gamers;
JSimpson is the standout example.
It seems to me #3 is the kind of thing you're looking for. Here's my analysis of the prospects:
- There are definitely people out there who would love to play RPGs again but don't have a GM to run a game for them or a group to play with. Most of those people are going to have entered gaming around the peak D&D years of the early '80s, so they'll be in their late 30s, likely to have kids and careers but not free time or friendships defined by gaming.
- You're not going to reach those people by posting at RPG forums. NYC is a gaming-rich environment, and anyone who is close enough to the gaming scene to know about a D&D Meetup or RPG.net is going to be able to find a group without paying for the experience.
- Your pricing is so low that it becomes a turn-off. Let's say you have six people at the table. You're valuing your time at about one-tenth of the amount they're each paying a babysitter so that they can go out for the evening. You need to have the confidence to charge the kind of rates that other skilled professionals do.
- Consider renting a space. Cafe 28 is a good location for gaming (I play there myself, drop me a PM if you want to get together!) but part of what you're selling is professionalism and high-end quality. For Ken Hite's excursion, we rented a suite at the Hotel Intercontinental (one of the occult sites on the tour, as it's a former Masonic temple) and had them cater a meal. In NYC, I've heard that the suites at the W are a good option. Including things that have obvious value in the package makes it an easier sell than your GMing time alone, since gamers don't usually pay for that at all. Yax's
Epic Vacation is a great example; it'll be interesting to see how it succeeds!
- Tipping is problematic. Jonathan Tweet told me he'd been thinking about playing for tips as a route to professional GMing, but that it'd all fall apart the moment the biggest tipper found an ultra-cool magic item. Making it anonymous (maybe a Paypal button on your web site) would keep other players from being suspicious that the big tipper is getting favorable treatment, but it leaves open the likelihood that the tipper himself expects to get something special in return.
- Having a website is a great idea. Playing and DMing more is also good. Basically, everything you can do to establish yourself as someone who really enjoys gaming is important, because the only thing reward you can count on from doing this is your own fun and satisfaction.