Worry about something that may never happen is a bad mindset that will only leave you with regrets in life. If you are healthy now is the time to enjoy yourself while you can. I came over here 2 weeks ago at 54, I have no idea what might happen or what I am doing. I am just winging it while I have the health to enjoy myself. If something happens, then I will deal with that if that time ever comes. If you want to live in Thailand then try it. If you hate it, you can always go back home. If you love it, then everything will be all right!
I would make sure I was financially secure before making a move based on your situation...if you don't have liquid 20k, I would be very cautious and make sure you aren't going to put yourself in a bad spot. I know it seems like a good idea and I am sure she is special, but man you need your financial ducks in a row.
I just came in on oa visa... have your insurance forms printed, your visa approval form, and that was all I needed to get in through immigration. Condo did tm30 for me...easy no problem