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Sorry for the delayed response. A social gathering group sounds like it would be a good idea for you. Before starting your own, you might want to look into whether one already exists in your area. I would search from some national crossdressing organization to make sure that it's a reputable & safe group. I'm not trying to sound judgmental, but one could argue that cross-dressers aren't quite a part of mainstream society (although, luckily in some more open parts of society they are more accepted); so I would just want you to be safe. Do some research and make sure you're not getting sucked into some fake group (e.g. con artists or cult).
I do not know much about meetup.com so you're on your own there.
I don't think there's any harm in applying for the job you mentioned...but be prepared for the worst possible outcome of rejection. I always say "hope for the best, XXXXX XXXXX worst." And I'm not sure if it would be best to be upfront about being a cross-dresser or whether you should just go dressed as a woman if you think they won't figure it out. I really don't like telling patients or clients to not be honest...but in a potentially judgmental world, it may be the lesser of all evils...your privacy is your privacy. The flip side is if they hire you thinking you are a woman but later figure out you're not, it could come back to haunt you. You may want to consult a legal expert of employment & discrimination on this matter.
I hope this helps...good luck.
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