Comanches are great deals. I have never flown a 250/260, but I've got about 5 or 7 hours in a Comanche 180 (my instructor's plane bought brand new by his dad in 1962). I'm not sure I understand what people are complaining about with the landings on them. I find it no more challenging to fly than the Mooney M20F I fly, which I don't really consider challenging so much as good fun.
I would say check the useful load and see if it matches your mission. Otherwise, I really wouldn't see a reason to avoid it. Yes, you may have some insurance requirements, but most of those requirements are probably good ideas. You will also want to fly it a bunch, especially at the beginning, just to get familiar with approaches and landings. Once you get into this class of plane you do need to actually plan your approaches, patterns, and landings. For example, in the Mooney I was still 30 miles out when I started my descent yesterday. I also needed to descend 6000 ft to reach pattern altitude and that 30 miles was only a bit over 10 minutes. In the Comanche 250 it'd be even quicker. You'll get used to it quickly, though.
I know the 180s had a prop AD, not sure about the 250s. Either way, my instructor replaced the prop on his 180 with a nice 3-bladed McCauley. Looks much cooler.