I spent about 10 years on taking the commercial route and also wasted quite a bit of my lifetime waiting at sh***ty airports for delayed planes or even worse - got shuttled long distances by Taxicab, when flights got cancelled (in my case that was always a matter of airport closing hours due to "noise" reasons ...).
My requirements profile changed a bit, when I had more influence on the places to go. If you have a need for strange locations and want to stay commercial pax, wait for the upcoming renaissance of the regional airlines.
In my view, you don't need heavy equipment like a King or JetProp. You get along pretty far with Beech F33 or even C182s, with some restrictions even 172s will do most of the jobs.