I only have the Cub now, but I had a 250 Comanche which was a great traveling airplane. I don't think you can beat them for the money. At the same time I had Great Lakes 2T-1A-2. Fun and the easiest taildragger I ever flew. Living in the Northeast, it spent a lot of time in the hangar. Open cockpit only works about 7-8 months. And as I got older, that number was getting smaller!
Before those, I owned a J3 and a 1958 172 with the Bolen TW conversion. It was a straight tail 172, so most people thought it was a 180 until they got close to it. I also owned, with a partner, a 1940 Fleet 16B that had been modified with a 220 Continental in place of the 125 or 160 Kinner. It was a performer. It was called the Flaglor Hi-Tow, built by Ken Flaglor of early EAA fame in 1957. He used it to tow gliders. It is now owned by Dr. Brent Blue who writes for AVWEB and other places. When we sold it to him, it need a lot of work and he did the right thing and had it totally overhauled. Most of the work was done by Aviat.
My first airplane was a T-Craft. Bought in 1974. Recovered it my self in 1980. Sold it in 1984 when I bought the Cessna.
Other A/C I have ferried for friends include Super Cub, Top Cub, Huskey, Stearman, Waco UPF7, Waco YKS7, Waco UBA. Loved them all!!!