CTB - LWS : Plane for the mission? Pilot for the plane?

Hi Folks

I am a relatively low hour PP-ASEL(about 90 PIC, half in C-177 / 152, the
rest in Challenger AUL and gliders, total time, including dual = 160
hours). I have not been flying for several years, but am in the process of
regaining my certification.

As the only way for me to be able to fly from where I am located means
ownership, I am in the process of making a shortlist of airplanes I would
like to consider.

Part of the mission would be fairly regular flights from CTB - LWS and
back. (2-3 souls and luggage). What straight-legged 4 seaters would be up
to the task? (The actual route would be CYBU - CYXH - CTB - LWS )

Crossing those rocks would seem to exclude a C-172 and its friends. It
would seem that something of the order of a C-182 or Piper Cherokee 235
would fit the bill. Does anyone here have experience of flying this kind
of trip in, say a C-177, or PA Cherokee 180?

Would I have trouble finding insurance if I went straight to a C-182 or
PA-235? From what I have read, that should not be a big stretch for me,
and would make crossing the ridge a lot easier.\

All VFR for now, although I intend to pursue a IFR rating later.

Thank you for any and all replies.

Steve