I agree with Steve on buying the best equipped plane you can, regardless of the type. When I bought my '79 185, I had about 5 hrs in a 140 but that was 35 yrs earlier, but got a tailwheel indorsement in a Husky as I purchased my 185. My insurance company required 5 hrs in the Skywagon, but for me, I wanted and received 2 more sessions with an ex MAF chief pilot and that was a huge improvement for me. There is no question that a tailwheel plane is more demanding of the pilot than a trike plane. I land in crosswind conditions as I find them but definitely am on high alert for ALL ground operations. For the value of the plane, I didn't think that insurance was drastically higher than a trike plane.
Now, with 1,000 hrs in a Skywagon, I feel comfortable with some comments. First, the narrow cabin sucks. Second, it is relatively slow as a cross country plane, and I fly from BC to Mexico and back twice a year and bitch about the speed every time. For me, the only value of a tailwheel plane was for the float application and in hindsight, I would definitely consider a 182 or 206 for my mission and I have owned both of those planes before. I have no "macho" tailwheel need and therefore would most likely not own a tailwheel plane if not for floats. I also do not fly into places where the benefits of a tailwheel plane are great. A very high percentage of Skywagons have been ground looped. One must carefully examine the plane and ensure that any repairs were done correctly. Again, this holds true with any plane purchase.
The good things about a Skywagon is that it is a Cessna. Everybody can work on the plane and parts are readily available. A 185 can carry about anything you can stuff in it but loading is more a bit of work but no different than a 182. I do love the baggage doors on
a 206. The flaps require some strength to pull on, my wife needs two hands to operate the flaps. Yanking the flaps are an advantage on floats to pop of the water. I don't know if this translatres to ground operations on wheels as again, I haven't needed to do this in my flying.
I guess you need to give some thought on your mission, your wants and more important, your needs. Pay attention to what guys like MTV and Gump have to say as they have long historys of practical experience. Good luck on your quest. FF