@Daniel ******
As far as "retirement visa" options you have these;
get a 90 day single entry Non-O about 2000baht
come to thailand get a one year extension 1900baht, get a re-entry permit 1000baht <- that lets you leave/return ONCE and keeps your extension alive
get a year-long, multi-entry Non-O-A $200USD
come to thailand get stamped in for a year, have unlimited exits/entries during the year validity of the visa always getting stamped in for a completely new calendar year when you enter.