@Derek **********
Don't think too much. Don't waste your time and energy.
I see you meet all the requirements for a no brainer. You're in a perfect position.
Come to Thailand on a 30 days visa exemption (free, no visa) or with a 60 days visa (you can get from the local Thai Embassy in your country) and go RIGHT AWAY to a well established visa agency after arriving (just check facebook and the reviews they get, it will take you 15 min to pick yours, regardless of where you'll reside in Thailand).
Let the agency handle your first Non O visa based on retirement (that's the real name of it, but don't bother). They will do EVERYTHING for you, for a cost of course, and you'll learn everything needed for the whole procedure. They'll also set everything required for you (like a bank account).
So the next year, for the renewal of your Non O visa, you'll already have everything set up, everything in order. You will know all the requirrments and specifics for the visa and do will be able TO DO IT YOURSELF, for no additional cost than the visa itself (1.900 Thb) this time.
Using a visa agent is the best and easiest way to do it for a first timer.
In your position, the Non O visa (that you only get and apply for once HERE IN Thailand) is not only the cheapest, fastest and easiest option, but it's also the only logical one.
Go enjoy your new life.
Take care.