Towing Travel Trailer and Boat??

I have a 26' Bumper Pull Travel Trailer and a Supra 21v and I'm tired of trying to find somebody else to pull one or the other when we want to go somewhere for the weekend. I know this can be done but how safe is it with a bumper pull travel trailer?? I know some of you guys are piggy backing but not sure if you are with bumper pull.

I'm in Texas, travel trailer has elec. brakes on all 4 wheels, boat trailer is tandem with inertia (sp?) brakes and pulling with a 3/4 ton dodge cummins. The travel trailer has weight dist. hitch and sway bar, even though I usually don't need them, I'm sure I would in this case. I think our legal length is 75', I'm sure I would be close to that...

What hitch would be good for the travel trailer? receiver? I think my TT bumper is bolted directly to the C-channel frame, I need to double check that.

Thanks for any input, I'm just kicking this idea around and wondering if it's worth pursuing.