Due to BasicMed and my own weird personal preferences, I want an airplane with the following characteristics:
Vne 250 knots
Ceiling 18,000 feet
Tandem
Tailwheel
Retract
CS prop
4 hours endurance + reserve
450# full-fuel load
Anything out there that meets all these reqs?
Found one
https://en.wikipedia.org/wiki/Curtiss_SB2C_Helldiver
Tandem
Vne 256 kts
Retractable main gear with tailwheel
Service ceiling of 29,400 feet
Can go 6+ hours with 1,000 pounds of bomb (or luggage)
Constant speed prop
Bad news is there is only one airworthy, and I'm pretty sure the CAF isn't going to sell it to you.
That's quite an interesting (and contradictory) set of requirements you have there. Tailwheels are found on pre-1950 designs, and sporty or utility modern designs. Tandem seating is found on small lightweight designs, and some military usages, but the military moved on from tailwheels in the 1940s. As long as you are tucking up the feet, you might as well go with trigear and skip the groundloops. Think about it, with retractable conventional gear, you have the opportunity to land either gear up or ground loop on every landing. It doubles your chances of showing up on Kathryn's Report. The 250 kt Vne maps to a traveling machine, but those are going to have trigear, and very few will be tandem.
If you're seriously wanting to buy an airplane, the T-34B Mentor is probably the the closest you're going to get to checking all those boxes. I'm not sure there's a place for baggage in a Mentor, so if there's two of you going somewhere, a Bonanza would be a better fit.