I have been biting my tongue while reading this thread because I figured it might be a bit too self serving to respond but some of these responses have gotten pretty silly so here it goes...
To the Original Poster welcome to San Antonio, while the community here is probably not what you were used to in MA, there is a lot of exciting stuff going on in the community. The city is growing quickly and of course a percentage of the population moving here is gay, so the gay community has the potential for some dramatic growth as well.
My partner and I are the major property and business owners of the gay oriented businesses located at Main Ave. and Evergreen in Tobin Hill. We originally opened HEAT nightclub 6 years ago and over the last 2 years have been buying the surrounding properties.
We are trying to develop the area into a viable gay neighborhood.
There are two components that can be found in successful gay neighborhoods around the country.
The first is a vibrant business district. The area is currently comprised of 4 bars in a row. Historically bars have always been one of the social centers of the gay community (think Stonewall) but of course more is needed to appeal to everyone.
The leases expire to 2 of the businesses there (Saint and Silver Dollar Saloon) in about a year and a half. Our future plans involve redeveloping the center into a mix of retail and restaurant uses. There will probably still be a bar or two included in the plan, but on a much smaller scale. Also a coffee house will almost certainly be part of the plan.
We are currently working on renovations to Luther's Cafe across the street. Luther's will retain its original Texas burger joint appeal while expanding the menu and dining area to accommodate a dinnertime and late night business.
Currently there is no "gay" restaurant in SA but Luther's will fill that gap. The goal is to create a place where someone can bring his or her partner for a birthday dinner with their friends without worry of rude comments or looks from others parties.
We have worked closely with the city and this past year were able to get much needed replacement to the sidewalks and curbs. We have planted 24 mature palms and additional landscaping is on its way as soon as we have the last freeze.
The second aspect that most successful gay neighborhood have is that they are almost always located in older parts of town. Obviously the neighborhoods were not always gay; but they were at some point considered less then desirable and the historic housing stock was appealing to people with the money and desire to invest and improve the community. Perfect for gay professionals and couples with money and no kids.
Tobin Hill was recently designated a historic district and, while the houses are not as fancy as those in Monte Vista, it has the appeal of being an area that hasn't been "discovered" yet and the houses there are still extremely affordable. Dallas' Oak lawn (20 years ago) is a perfect example of the type of neighborhood that is appealing to those with a bit of vision. Then it was run down and seedy, now it is one of the most desirable neighborhoods in the city. San Diego's Hillcrest, San Francisco's Castro and Houston's Montrose have gone through similar transformations.
Another promising sign that Tobin Hill is on the brink of a renaissance is the recent interest by developers in building on vacant lots (infill development). Check out the link below to see the houses that have already been built in the neighborhood with plans for more to come. These are high quality, stylish houses that are selling for a good price.
http://brownstonesa.com/index.aspx
Also the recent purchase by a local developer of The Aurora Apartments on Crocket park has the potential to turn it into one of the most desirable addresses in the city. The Aurora is a 20 story art deco apartment building built in the 20's. With the right development plan (and a LOT of money) it could turn into a very exciting place.
It might be interesting to note that even on the small scale we have here, Austin has no neighborhood comparable to what we have in SA. The warehouse district has 2 gay bars (OCH and Rain) on 4th and that is it. The rest of the gay oriented businesses are scattered around the city. There is a more affluent and socially active gay community there but I would by no means say that it is any bigger. It is also much younger (college kids) and transient.
Of course its as impossible to compare the gay communities of Austin and San Antonio as it is to compare the cities themselves.
Sorry for the long post but i thought this info is germane to the original question... Consider looking for a place in the Tobin hill area, you may be able to say someday you were a pioneer in the transformation of a great neighborhood.
Welcome to San Antonio and I'm sure you will be impressed by the friendliness of the gay community here as well as around the city in general.
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