Hey Charles,
For some reason, your situation really resonates with me. I've read this whole thread from start to finish 3 times, so far. I mostly want to give my own answers and guidance to as many points as I can. Please ask follow-up questions if anything's unclear.
First I want to say John Woffindin's answer seems very interesting for your case. Definitely a +1.
And before I get into all of my points, sorry for the Markdown, but I really have to go to sleep now. No way I'm taking the time to format all that in Gmail :-)