@Chris *******
you need to leave and re enter Thailand every 90 days on a METV to get a further 90 days (60 visa + 30 day ext).
When you apply you need to prove you need a METV and not just a single entry visa. To do this you need to show a ticket leaving and re entering Thailand within the period of travel. If you don't provide this the embassy may just give you a single entry tourist visa instead, but keep the METV fee which is more expensive.
Pretty sure you can only apply for a METV in your home country. To stay for an extra 95 days to make it a year, just use a border run company. They grease the wheels with immigration so you can get a new stamp without hassles. You can do this twice by land per calendar year. Each will give you 30 days visa exempt which you can be extend by 30 days. That should give you enough time to see if retiring in Thailand is right for you.