Jamesqf - I think your situation sounds sensible, but our OP, Stretch, doesn't drive much at all (unless I'm missing something?).
Also, I look at everything through the lens of where I am, NJ. Insurance here is astronomical.
My Jeep (93YJ Sport) is sitting in my garage, unregistered and uninsured because it wasn't suitable to carry my son (trust me, no exaggeration there) when he was a newborn/infant, and now it would only be a gas powered toy. We replaced it in MMM fashion (used, high utility, low mpg, low price, paid cash), and just don't NEED it on the road, and its in such a condition that it won't command a decent sale price, although its functional. If it were cheap enough to insure, I would be out with it a few days every summer and winter. Registration + insurance, without collision, would probably be around $800 for the year and my wife and I have relatively clean records. And you can't just decide drop insurance here, you would have to turn in your plates as well.
Long term plan is to fix it up, make a father son project out of it... we'll see. It would also be fun to go diesel, or keep the monster I6 and set it up for homebrew ethanol... its fun to dream! Electric seems way out of the park for me, although people have done it.
theSchmett