My first tailwheel plane was an Aeronca champ. It is still the airplane I have the most hours in. My next airplane was an RV-4. The tailwheel RV's are probably the easiest TW aircraft to handle. They just land straight and track straight. But with the Champ you could drop it in and it would just mush around on those oleo gears. If you drop an RV in you'll bounce about twice as high as the height you dropped it in from. I'm flying a Rans S6 now and it has the same spring steel gear as the RV so is not very bounce tolerant at all.

Everybody loves the Cubs but T-Carts are very good planes too. Also, if you're looking to get into TW aircraft on the cheep, don't overlook the Aeronca Cheif. Probably the cheapest way into the air there is.

I'm surprised no one is promoting the LSA tailwheel products here such as Highlander, Rans, or Kitfox. It's not the cheapest buyin but used Experimentals are available which give you the freedom to lower your maintenance costs drastically along with your parts cost, great short field performance, and 'almost-new' reliability. All things to consider.....