Thanks for the replies! My mission is developing. For the first 100 hours or so, I'd anticipate it would be just me in the airplane. I'd like to earn my instrument rating. Typical flights will be from Memphis to DFW, STL (where my son is in college, WashU) and wherever my daughter ends up choosing for college next year (likely somewhere in NC.) I don't see me doing anything super long distance, but who knows. I'd rather solve for 80% of the mission (just me in the plane or perhaps me and my wife, <400nm) than overbuy capability at this stage in the game. If we find that everybody loves flying as much as I do, then I can start thinking about a big boy plane.
I've been limiting my search to Lycoming 4-cyl powered certified aircraft in the $50k purchase price range that would have a clear exit strategy/market should I decide to upgrade after flying for a couple of years. That's led me to a 172, a M20x, or a PA28 of some flavor. The M20's speed seems like it would lend itself to being more "upgrade proof" than a fixed gear Cherokee 180 or certainly a 172, i.e. I could see being inclined to keep it longer.
Cheers,
Brad