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Of your top tier, Wayland is nowhere close to your price range. I don't know about commuter rail in Southborough, Ashland or Hopkinton, but I'm sure they're all significantly more than 45 minutes to Boston. Of this group, Natick is your most likely bet. I'm not sure about commuter rail, and it might be a squeeze to find that house, but I think it exists.
Second tier, Newton is completely out of sight for housing, and otherwise is perfect for you. Maybe a condo? I don't think Framingham would suit you for school. West and Northborough are further than 45 minutes (don't know about the train).
Last tier, Sudbury is way too expensive. Hudson and Holliston aren't famed for their schools that I know of, and I don't think they have train access. Marlborough might suit- don't know about train access. I think Boston, realistically, is further than 45 minutes by almost any means, especially depending on what part of Boston. Will you be working in Boston, or only looking at it for fun and recreation?
I don't think any areas of eastern Mass/greater Boston are particularly a problem regarding gay families.
Might I suggest my own town of Littleton? It's not "fun," but it's a very quiet, pretty, unpretentious town right between I-495 and Rt.2/2a. There is a commuter train (Purple line) that runs to Cambridge and then North Station in Boston. Your housing price is quite doable here. There's a lot of beautiful conservation land with trails and all, good library, and almost all kids go on to 4-year colleges.
I wouldn't say many people spend a lot of time going to the city, but you could get into Cambridge relatively easily (more the place for gay women than Boston, I think). Lots of family activities.
Also, how about Acton? Closer to the city than Littleton. Less small town, superior schools, more than one train stop with more parking than Littleton. One of the most ethnically diverse well-heeled suburban area, with villages within Acton. I think you could find your house there if you look hard.
Like I said, I don't think any town you or I mention is a gay-friendly problem, but I do think Acton is quite cosmopolitan without being pretentious. I think of Acton as being similar to Newton in its socio-political way (although less Jewish). If I had kids and/or were a gay couple, I'd certainly consider Acton among my first choices.
And oh, there's no fun nowhere except right in the city. Sorry.
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