Stick vs. yoke really doesn't matter. The stick is entirely intuitive if you've used a yoke before. As Whee pointed out, it could be a bit more challenging (for the first hour or so) going from stick to yoke. But it's really more about the rudder pedals. If you learn in a tricycle geared airplane, try to find an instructor with tailwheel time, and have him/her ride you about keeping in trim at all times. Let them know you'll be flying a tailwheel airplane someday, and don't want to pick up bad habits early on. Learn to lead your turns with the rudder, and to stay directly on the runway centerline at all times, and you'll be halfway to your tailwheel transition before you even start that process.
As for the airplane - it only matters that you buy something you can afford to fly, then fly the wheels off it... Piper Tripacers and Colts (108 hp Tripacer with 2 seats) are tricycle planes that are usually cheap to purchase, and usually cheap to fly. (I say usually, because any airplane can be a money-pit, if you don't do your due diligence, have a good pre-purchase inspection, buy a high-time engine/prop that needs replacement right away, or just get unlucky.) That said, buying a plane you want, with the avionics you want, but with a run-out engine that can be an excellent strategy if the airplane is otherwise exactly what you want/need, and you hold back the cost of the overhaul and plan to do it immediately...
To me, many of the early fabric-covered airplanes (Cub, Champ, Taylorcraft, early Citabrias) would seem to fit the bill, assuming the fabric is OK.. Some of the cheapest fabric-covered airplanes have fabric that is fine, but the paint is chalky and faded. As long as the fabric is good, those can be a tremendous bargain -- great-flying planes don't always have to be show-planes.
The thing to remember is that this isn't your "forever" plane. It's your "learning" plane. And just like with your kids, it's a lot more fun if you can afford to fly it, and maybe even fix something without having to take out a second mortgage on the house... My current plane (a 1965 Citabria 7ECA with O-200) looks ratty, but flies great. The fabric is original 1965 vintage, but still passes the tests every annual. It certainly doesn't draw a lot of admiring glances (nickname is "Rags"), but it is a safe, good-flying plane. I bought it super-cheap to earn my tailwheel endorsement, to have something to fly while I built a Bearhawk Patrol (2-place tandem) in my garage, and to build up some tailwheel time to help reduce insurance cost for when the Patrol is flying. It satisfies that mission with flying colors!