I would say research RV parks in the area to see if they even offer seasonal/full time RVing. Give them a call if your questions aren't answered on their website.
As far as size goes, think about that idea of getting a small trailer. You'll be living in it every day for 2 years. If more space is what you need, for $20k you could get a slightly used bigger trailer.
Do you plan on RVing more or full time RVing when you do retire? If so, do you buy your retirement rig now?
Andy
2012 Keystone Outback 280RS
2014 Chevy Silverado 3500HD 6.0