I worked airplanes around Alaska for a number of years. Much of that time was in Cubs, Huskys, 180's, 185's and Beavers. When the time came to replace a 185, a collective decision was made to replace it with a 206. That wasn't my first choice, but this decision was made based on logic, and the 206 won that argument.
After a couple months flying that 206, including on and off gravel bars and floats, I couldn't imagine having to go back to working a 185. Oh, I flew 185's after that, and I'm certainly not afraid of them.
When I moved to MN from AK, I looked real hard for a good 182. A few years ago, the market was pretty soft for 182s and you could get a really good one for not much money, but in the meantime, 182s became much more popular again, and prices went up substantially.
Then I got to MN. In much the same situation as you, only reversed, I'd have had to hand the state a bunch of sales tax $$ to go to a 182. If it hadn't been for that issue, I'd be flying a 182 right now, and happily.
Unless you are doing skis or some pretty hard core off airport stuff, the 182 is a great do-it-all airplane, in my opinion.
And, the first time you're stuck under one of those marine layers, fidgeting, you'll probably regret your decision all over again.
I have a 170 and it's a nice little plane. I GUARANTEE your 182 is WAAAAAYYY faster than my 170. So, you'll get places for less gas money than I can. The 170 might be a little cheaper to maintain, but they are all OLD airplanes, and things wear out. Seems like every annual, I'm replacing some basic item or two.
I'd take that $$ difference and put it to good use on the machine you have, and enjoy it even more than you have already. I'll bet if you ask around the right places, you can find a good engine guy who can field major that engine for less than you may think.
Either way, you probably won't go wrong.
If it was up to me, I could care less if I ever flew a tailwheel airplane again. There is no longer a mystique there, merely a liability.
Except on skis, and I've flown 182s and 206s on skis as well.
MTV