Well, I ended up deciding on a monastery in Thailand, but a year and a half ago I left my high-paying job in New York City to ordain. I’m happy to share my experience:
I had lived at monasteries for a total of about 30-40 days in my life (a weekend here, a week or two there… not including retreat centers) before deciding to jump. After leaving my job, I took about half a year to tour the world and try different monasteries. I stayed for about 8 days at a time at over a dozen monasteries in the US, Canada, Asia and Australia. I observed and evaluated each teacher and community, took notes, asked questions, and tried to learn as much as possible about what I needed and was looking for. I stayed with some friends in California for a while at the end of my tour to decompress and plan next steps. At first I was thinking of spending a month or two each at my favorite few monasteries before making a “final decision” but a mentor of mine encouraged me to just pick one and stay there as long as I like. I picked one in Thailand and, a year later, I’m still here and still liking it.
RE healthcare: I tried to get government healthcare in the US after leaving my job, but being itinerant in a system where health insurance is state-by-state… it wasn’t really possible. Assuming you have no chronic health problems, I recommend just going without insurance for a while. This was a bit frightening to me at first, but eventually I realized that over the counter medicines in the US (and clinics in Asia) are really cheap and are far better than even the best medical care a few hundred years ago. Just take it as a practice in renounciation and being content with what’s available.
RE paperwork: There’s not much. I’ll echo the above about the people at each temple knowing more. Each community (and country if you go international like I did) will have its own thing. Just read the information online, ask around when you visit and you’ll figure it out.
The only critical thing I did before setting out was I took the time to get my family on-board. I spent a while living with my parents over Christmas to explain my decision, what it would mean, how they could help, to get my parents’ permission, etc. That was tough, but it has been very helpful both practically and emotionally.