I've got a different bike with S&S couplers, and while I've enjoyed it immensely, I'm not sure I'd buy it again. Mine's more a play bike than one intended for long tours, and it's a bit difficult to pack a large (~60 cm) bike -- mostly because I insisted on getting the bars up where I can reach them, which means packing the fork and bars in the case gets difficult, and partly because of the breakdown that's necessary. I have to take off the cranks, seatpost (with saddle attached), front caliper, fork, stem, and bars, deflate both wheels, and the TSA inspectors don't mess up the careful packing if I take the front tire off the rim. If I had it to do over, I'd go with 26" wheels and small slicks.
I can pack or unpack in about 40-60 minutes each way. When I was going to a town for 2 weeks, it was easy to justify. Now that the job has changed, most of my trips are 2-3 days. It's a bit of a hassle to assemble, then pack, for just one or two rides.
(Take a couple pairs of cheap rubber gloves to wear when unpacking or packing. They'll save a lot of dirt and grease cleaning.)
Now to your questions, there's not necessarily a lot of mechanical ability needed; the stem adjustment is the only critical thing, if you can figure when to stop tightening the other bolts. The big S&S wrench and 5 allen wrenches, plus a pump, are the only tools I need.
If you're going to use this bike for multiple tours or trips, it becomes much easier to justify the price. For one trip, I'd suggest you ship it ahead to a local bike shop at the start of your trip, and have them assemble and tune everything.