Hi Dave,
I did about 450hrs glider towing and have yet to hear of a twin being used, besides it sounds a little excessive. With regards to the parachuting, that's a maybe, though I think that instructing is probably the route with the greatest possibilities. I’d have thought that you'd probably need to do some SE instructing before being allowed to do any ME - only a guess, I'm not an instructor.
regards,
h_k