If I have about $100k to replace my 337, which should I buy and why?

[Roger]

I believe that what you may save in purchase price on a pressurized aircraft, will soon be "eaten" by maintenance This for any aircraft, not just a 337.

Not only that , but one has to also consider that the more complex an aircraft, the more possibility for various failures during regular operation, thus the safety factor may well be decreased with complexity. After all, the many things that break don't wait to do so on the day of the annual (or 100 hour).

Your mission profile would seem to indicate no need for pressurization, or for that matter even a turbo.

Good luck with the search.