For long cross country flight I prefer a nosegear aircraft or retractable for that matter. For unimproved landing strips, definitely a tailwheel.
I have flown the early and late model 182's, the best one I ever flew was a late 50's model, 1957 I think it was. The thing sat high enough that you could taxi it through cattle guard gates if you needed, was very light on the controls and a joy to fly.
Tailwheel aircraft demand a higher degree of performance from the pilot. Lazy, sloppy and less coordinated pilots are weeded out fairly quick in them. Tri-gear or Land-O-Matics as Cessna called them, allowed many people to become pilots that wouldn't have made it to a license in a tailwheel.
For
real unimproved short strips I prefer a Super Cub because I can get into and out of places aircraft like a C-206, C-210 and C-182 can't go.

The fact that it is a taildragger is less stressful when landing in new places with tall grass which may be hiding ruts, rocks anthills etc. Someone said it elsewhere on this site, if your landing in a place like this in a group, let the tailwheel aircraft land first to find the obstacles that would turn a nosegear aircraft into scrap aluminum.
Some people on here describe an unimproved strip as anything dirt 3000+ ft in length. To me that's JFK. In that case why limit yourself to just Cessnas.
Adding to JR's analogy of dirt bikes. There are people who want to ride in the dirt and take a street bike, remove the lights and add knobby tires only to be sorely disappointed with the results compared to a real dirt bike. Sure it will work to some degree, but you will never have the full utility your looking for. On the other hand would I want to be touring the highways on a dirt bike, not likely. Pilots should do some soul searching before they buy, figure out what kind of flying pleases them most and purchase accordingly for that specific purpose.
As far as the King Air pilot/CFI, chances are he progressed through the ranks in tri-gears and never sat in a tailwheel aircraft. Funny thing is a lot of the professional carrier pilots flying the really big stuff buy small taildraggers to regain the feeling of really flying.
