Awesome, thanks for the detailed info. I've found some useful videos for bike maintenance and repair on Youtube but, like you said, the best way is to just give it a shot. My front tire appears to have a slow leak, so I'm going to replace the inner tube for practice as soon as I get the tools I need. Really, that's my main concern with doing a long ride; being somewhere on the trail and getting a flat from a sharp root or some stones and having to walk 15 - 20 miles because I'm not able to fix it on the fly.
I looked at Race Pace's clearance sale a little while ago and I just don't see anything worth buying. I mean, my current Trek 820 is great and it took a lot of punishment last summer without any problem. Really, the only complaint I have about it is how heavy it is (compared to some other Treks. My friend has a better/newer model and his is noticeably lighter), but even that is super minor and isn't a real problem for how I use the bike. Looking at Race Pace's prices, I can see lots of $499 and up bikes, but I imagine those would be marginal upgrades, at best. I don't have the money to spend near a grand right now, and I'd rather not do a minor upgrade when my current bike is performing perfectly well for my needs. I'd rather save up a bit and, if/when this one dies, upgrade to a really nice one for a grand or more.
In terms of logistics, I'll probably do it some time in July. I'm thinking of taking a Friday off work and doing it at a fairly leisurely pace starting Friday morning and ending Sunday afternoon or evening. Basically, I'm going to follow the Three Day "Econo" Option
here. I'm a sucker for history and I love taking pictures, so I'd like to make sure I have enough time to stop and smell the roses, so to speak. I'm going to try to have someone drive down to the staring point in D.C. with me, drop me and my bike off, and then take my car out so I don't have to worry about parking. Ideally this person will also meet me at the other end on Sunday to give me a ride back. If I can't get anyone to drop me off on a Friday morning, I'll probably park at Reagan National and take the Mount Vernon trail up to the Towpath's start. I shouldn't have a problem getting someone to meet me and give me a ride back.