As a tow pilot myself, flying a Pawnee I find the insurance requirement to be a bit off the center line. While a 500 hour total time requirement is reasonable, the requirement for 150 hours of tailwheel time can be deceptive. One could have 150 hours and 75 or 150 landings if they are flying cross country, perhaps less. In addition some insurance companies prefer you have 5 hours in the Pawnee before they insure you. Once you get into the air, airplanes are the same, it's the landing of a tailwheel that requires practice and proficiency. I'd rather have someone with 20 or 30 hours and 200 or 300 or more landings than a high time guy with fewer cycles. In the last year I've flown just short of 300 hours with over 2000 tows. Insurance companies might need to rethink these requirements. JMHO. (as taildraggers go, the Pawnee is quite docile)

Walt