We also have a Tandom and I concur with Lone Wolf's assessment. I'm not sure what Hobie had in mind with the Outfitter. It is shorter, fatter, looks more cramped, has a (100lb.) smaller payload and is probably slower. On the other hand, I think it has the capability to reposition the aft seat forward for single paddling and may have a more stable hull design. I have not tried it.
The Tandom is easy to handle solo, but works better with some ballast in the bow so it's less wind sensitive. I've made up some ballast tubes for such purpose.
The Tandom is managable with one person, but it takes a little practice to discover the best way to handle it. I lift it by the drive slot (from the bottom) with one hand and the cockpit bulkhead with the other. How you set it on your roof rack depends on what you have. I have kayak mounts for my truck's lumber rack -- no trunk (boot?) to worry about!
The wife really likes it, by the way. When she's happy, I'm happy!