*Leah and I only have one pickup but two gliders and tend to
like to go places together. *I'd like to solicit opinions (dangerous
thing to do here!) on how you would design a trailer to fit two
gliders, namely two Cherokee II's.

Have you checked with the Willat family? They took a motorhome,
and it seems to me (if I remember correctly) one trailer, one
motorhome and
three gliders....if ANYONE knows how to do it, it would be them!