Does this thing even exist?

The F1 Rocket is the aircraft closest to what you posted. 239 knot VNE so 11 knots short and has fixed gear. There is a new wing that should be released shortly which may be offered in a retract version. They are fantastic aircraft and as a result can be pricey. There is one near RDU offered at 186,000.
 
I think I saw a tail wheel Siai Marchetti parked at a local airport recently. I didn't know they existed either. Will snap a photo if it is still there.

Brian
That’s interesting. When I was investigating the build of a Falco (same designer, Stelio Frati), the landing gear could be built either way.
 
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Ooops. Staggerwing, and Spartan, cool planes, but I missed the OPs tandem requirement. I suppose you could just have any passenger sit behind you in the rear seat?
 
This might be close but no kit as of right now.
Prowler Jaguar

iu

https://en.wikipedia.org/wiki/Prowler_Jaguar
 
Re tandem: I just prefer centerline seating. But the Exec and Stag are just so freaking beautiful that I could overlook it for them.
 
Questair Venture - except nose wheel and not tandem. But it will do all the rest.

Oh, except that 4hr range only needs to be about 2 with it!
 
T-28s are too heavy for BasicMed. T-6 meets some of the requirements and is within the BasicMed weight limit. Speed would be the issue. Good luck with insurance.
 
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

s-l1000.jpg


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.
 
I'm thinking GameBird might fit the requirements.
 
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