I have a friends in a similar situation. They do successfully ride a tandem together, but they had to get it custom made by Co-Motion, one of the best tandem manufacturers. Standard off-the-shelf tandems are almost always designed for a larger captain than stoker.http://www.co-motion.com/index.php/tandems/general/custom
If you go this route, it is best if you work with a bike shop to get the measurements to custom fit you. If the bike shops are willing to work with each other, you should each be able to go to your own local bike shop. I'd recommend you visit one of the Co-Motion dealers in your area. You can find one by clicking on the "Find Dealer" link at the above cited web site.
There are a lot of options depending on whether you want couplers, belt drive, Rohloff hub, etc. Plan to spend in the $3000-$6000 range, maybe more if you go fancy.
Tandem bikes can fit on standard rear hitch racks, usually with the wheels removed to make them shorter. They can also be transported on the roofs of SUVs or station wagons. You can fly with a tandem by breaking it down if you get couplers, but it takes a long time to disassemble and reassemble, and you should buy the fairly pricey cases they sell. It will take two cases to hold it.
AFAIK, there's no problem pulling a trailer with a tandem. You can also use panniers if you prefer.