Wow, a lot of the things you mention resonate with me. I FIREd about 2 years ago primarily on the income of my commercial and residential real estate. I moved out of Dallas (thought I was tired of the big city) to a small town about an hour away, as I could buy a nice cottage style home on a golf course for ~$100K. Spent the first 9 months rehabbing the house - now I have a home base, close to family, beautiful surroundings, etc. Plus the free golf is nice.
Then did some travel. Read a ton of books. Do Crossfit and cook healthy. Found a nice girlfriend.
But saying that, now I'm asking myself...what next?
I had planned on traveling ~6 months of the year, and I may still do that, but traveling alone gets pretty...well....lonely. And I'm lucky in that I've done a ton of international travel over the years, but that also means it's not as cool as it use to be. At least to me. I've thought of RVing around the US some, so that's an option, but I've hit most national parks that I want to see and been to most of the big cities, so I'm not sure I really need an RV for my US travel.
I also considered learning Spanish, but wondering if that's a lot of work for nothing, especially if I don't end up spending at least some time on an annual basis in a Spanish speaking country to keep the skills sharp.
Now saying all of that, for whatever reason I LOVE real estate, and could see myself spending 6-9 months a year buying properties, rehabbing them, renting them out, growing the portfolio. But I don't have the capital to do that without hard money loans, and I'm unwilling to go that route. So I've thought about going back to work part time (or maybe full time for one year) to provide the capital needed to speed up my RE acquisition. Or maybe I just wait, and in a few years I'll have the capital accumulated. Hell I don't know. But I want to be 'productive' and do something...
So saying all of that, my suggestions might be:
1) look into the commercial RE deal. I've thought about the same thing but never looked into it. I'm sure you could find a firm where you work 8-9 months a year.
2) consider moving to Boulder (love that city) for this gig. Take 3 months off a year and go somewhere in your RV. Somewhere WARM
3) consider buying a place in Boulder. Not because you need it, but because you'll qualify for the low interest owner occupant loan and can add a new property to your portfolio (of course, this assumes the numbers work, which in this market they may not). Get a roommate or two to share the costs until the year expires and you can rent it out entirely, repeat the process.
My other suggestion, if you're not ready to settle down is just give it more time and think on it a bit more. Move cities perhaps. Austin might be a good choice.
Meet ups are a good idea, I've tried a few, never really met someone but I'd still give it a try.
You may want to check out Art Of Charm - I think they're located in LA, might be a resource to meet some like minded guys (I've only listened to their podcasts).
Hope that helps~