Tow Pilot Checkouts, Rough-Field Tri-Gears?

All -

Do any of the USA folks here on RAS operate in a club without a 2-seat
towplane? If so, how do you check out new towpilots? Do you find
simulated towing acceptable training?

On a related topic: Given the dearth of Robins in the USA for tri-gear
towing, does anyone have suggestions on a tri-gear towplane that can
operate out of a rough grass strip? We now land on asphalt, but our
takeoff area has some broad swales and occasional mole-holes. It has
spawned legends of bent Cessna firewalls; so a 180 or 182 seems to be
out of the running. Any alternatives out there that are capable of
hauling up a loaded 2-seater like a G-103 or L-23?

Thanks,

--Noel