[Edit - Removed]

Great airplanes. I loved mine.

Mike,
Have quite a bit of time in a 140 (owned one) and a little in the 170. The 170 has MUCH more utility and room. Some even have the STC for the larger engine which would make this plane a great performer short field. I found them substantially easier to fly (land) than the 140. The 180, of course, is a much more capable airplane but it comes with a huge jump in price.
Value wise, I think you are on the right track.

A C170 with a 180HP engine is a favorite among backcountry pilots. Very good performer with light loads, ie, pilot plus two pax. Cabin is a bit narrow for jumbos like me.

A PA-22/20 (Tri-Pacer conversion to conventional gear) would be another option to consider.

If you have flown a cessna 140 then you might have a feel for how the 170 handles. It flies like any other cessna (such as a 172) but like you said, the cool factor is way higher since it is a tailwheel airplane. Cessnas have the worst ground handling of any mass produced tailwheel aircraft in my opinion. I much prefer something with oleo or bungee type landing gear to leaf spring gear for tailwheel operations. Those springs can be a handful when windy and their mushy wallowing doesn't inspire confidnece. That said, the Cessna flies OK, is easy and cheap to maintain, and is available for a reasonable price. I have always thought that a 170 with a Lycoming 180 conversion would be the type of airplane that a man should never sell. It would do so much so well that it would be impossible to replace. If you can find a 170B they have 172 style wings with the nice big fowler flaps and single struts.

Yes Yes Yes... plus the 180 engine.

Just try and find one. You are right... if you do, don't sell it.

Thanks for all of the replies so far! I'd defiitely shoot for the A or B model to get the metal wings. I'm just starting to learn about these so I appreciate the tips. I'm looking in the 30-40amu range even with partners, so I have no hope of finding one with the O-360 180hp conversion I'm afraid. That does sound like a hell of a short field performer, though.

My wife has an early 172 (square tail) with the 180 and an early STOL Kit and 40 degrees of flaps. I have operated it on and off in just under 300 feet if I can get about 10mph of wind to work with. Fun, Fun, Fun!

If you're willing to own a vintage airplane such as a 170, why not consider an earlier model 180. Now you've got something you can have fun with, and really go somewhere with 3-4 people and bags.

A 170 with the 180hp engine conversion is cool, but a 180 with 230hp is better! Probably the best airplane Cezzna ever built is the 180/185.

Cannot go wrong with either a 170 or an early 180, but for the budget, you'll likely have more options with the 170. I owned a 1951 170A for a few years. Did a lot of the back country of Idaho as well as a lot of Arizona flying. Like a 172, it's a dog with four people but a fine performer with two. It has the best forward visibility of any tailwheel airplane I have flown...no need to S-turn while taxiing.

My current plane, for the last 11 years, is a 1977 180K. Handles like a truck compared to the 170, but, oh my, what a performer! It has the Kenmore ATC for the 185 takeoff weight (3,190 pounds vs 2,800 pounds stock) and, for the last four years, has the Air Plain's IO-550 300 HP STC with an 86-inch McCauley three-blade. When I bought her, she had the P-Ponk 0-470-50 (270 HP) engine STC and I registered her as N184TC 'cause it was almost a 185. Now, with the IO-550, some friends say I should re-register as N187TC, since it's more plane than your typical 185.

Mike:
It's got a nosegear but I have a friend who'd like to sell his IO360, 180HP 175. Constant speed, reasonable avionics, STOL kit. Enthusiastic flyer and not expensive.
PM me if interested.
The 170B with the 180 Lyc would be a fun airplane to fly.
Robin White

Damn, I bet that thing gets up and climbs like a rocket! Got any pics to share?

Here're a couple:

+1, particularly if you get the 150hp model - faster than similar vintage Cessnas. They are also great airplanes if you need to come down in a hurry.