It seems to me that these ideas are frought with CFR, legal and
insurance issues and the line between a club a commercial operation
would be crossed.

i dont know about insurance issues, but there is no reason why a CFI
of any type cannot be paid for instruction or a commercial pilot can
be paid to give a local sightseeing ride. and as long as the towpilot
is commercially rated he can be paid for the tow. I dont think the
FAA cares if its a commercial or club operation. the same rules apply.

Im with Matt on this one. I love to teach and give rides in gliders,
but if I walk across the runway (literally) to the power FBO i can
make some measley money. as much as i love soaring and teaching
soaring, i also love fresh ramen noodles waiting for me at home.
thankfully for my students i insist on giving the same high quality
instruction whether i get paid or not.

when i took my first instructional flight in a glider and Matt told me
'no charge' I was aghast. how could someone get training to be a
professional at anything and then not get paid? needless to say, in
return he didnt have to pay for any instruction on his way to his ASEL
certificate.

The only part of power flying that i've ever heard of that involves
free instruction is desperate young time building CFI's. In general
the practice is looked upon in a poor light. My power flying club
also aims to keep costs low, and CFIs are paid well and no one
complains.