Fun topic, I am actually stumped on this very question while looking for the next plane purchase.
Here a FEW items from my pro/con list.
-Wife & Dog LOVE the high wing getting in and out of and sight seeing.
-Husband has more fun flying low wing (more like Porsche than Suburban)
-Older passengers with creaky knees like high wings (50% of my friends)
-Mountain bikes & luggage like the loading on high wing (unless low wing w/doors like Beech 36 or Piper 6)
-Snow banks seem to like smacking around low wings a lot faster in michigan than high wings (especially this winter, and I'm from Michigan)
Currently I am at odds with what I would like and what fits my missions.
I want something cool like an old V35 Bonanza but the wife really wants something practical like a 182 (177RG is kind of a compromise) , and since 70% of my flying is with her I need to take that into consideration.
(and yes I do like Ed's Comanche, but cannot afford it since he got it all polished up, I heard it looks 30years younger and 20k more expensive after the Brazilian wax job )