I wouldn't hesitate a moment on a 185 as a first taildragger. Buy your last airplane first. Don't get something smaller first as you'll figure out the 180/185's are not hard to operate. I had 180, and it was very predictable and never surprised me. Crosswind landing in any taildragger will test you, and the 180/185 is no different

I would not hesitate to have a 185. I have limited experience in one and so far its been fun. I got an hours worth of taildragger intro in a Cub and the dual in the 185. So far, I have flown it 20 hrs and some 50 landings. Its fun, keeps you awake. My instructor said that a tail dragger must be thought out as having a snake on the rudder. It can bite at any time.
Once the wheels are off the ground its very similar to a 182 which most everyone praises. No vices.
Go ahead!!!

Rgs

Patrick

It is more like a 206 in the air.

Great airplane. Start on grass and you will be fine.
I have about 2000 hrs on my C185 since 1998 and they are fine aircraft.
Also the best ski & float plane you will ever fly.
Funny as I took off yesterday 5 min behind a Mooney and I smoked him in climb and he never Pass me in cruise either.
I was sure Mooney were faster than that.

Musta been an Economooney.

Some years are very "trucky" handling.
I've not flown the early 180s but I hear they handle more like 170s. Light-er controls.

A 1950s or 1960s big engine 180 would be light, powerful and have more nimblationess?

A '50's 180 with the PPonk conversion will smoke a 185 in take-off, climb, cruise and landing. Also much more fun to fly, and way easier to keep.
You can remove the bounce factor from the main gear by wheeling it on, and letting the upwind tire contact the grass, dirt, or pavement just a bit before the other.
The airplane, regardless of its condition, paint, interior, etc., will generate a lot of good conversation among pilots wherever you land.
Best,

Tom

I had a 185 with Robertson STOL. I would stay away from that setup unless you are an experienced tail wheel pilot and you need the performance. Because of the droop ailerons, the ailerons were very ineffective at low speeds. Cross wind landings, particularly on pavement, were a handful.