With a huge number of attendees to the annual gay pride festival and paradeAustin clearly celebrates the LGBT community. For the list, SeniorAdvice. I would include the Phlippines in this list. OP, I've no idea if it meets all of your requirement, but have you considered the Berkshires in Massachusetts? The city considered the most open is Manuel Antonio with a multitude of tours, bars, etc. Plus terrible weather 9 months of the yeat. I have the same question, OP.
No matter what happens with Obamacare, in NY we can always get insurance as was the case before Ocare.
As a community we are also less likely to have children and to be living alone. Lewes is about 3 hours from NYC I think? Some areas may be sketchy.
As a side note, funny enough we purchased our first hotel from a lesbian couple, the second hotel from a gay couple, and recently hired a gay manager.