My plans for a "Kindness of Strangers" tour

There are lots of weird thoughts that run through my head. "How can I complete the Transporter as shown in Star Trek?", "Can I write a series of books that will catch fire with 13-15 year old boys like Stephanie Meyer did?", "Why haven't I written my first symphony?", "It's great when I realize just how many people who I know only online are awesome", "I'd really like to see every baseball stadium", "Ooh, shiny!".

When I start organizing my thoughts, though, things fall into two main categories:

1. stuff that makes me tired (running, biking, hiking, etc)
2. stuff that could make me rich if I could ever follow through (inventions, creative endeavors)

Despite how silly I think it sounds, I can't shake one idea (warning, tangent approaching).

I've always told myself that, if I were independently wealthy with no great obligations, I'd hike the Appalachian Trail, solo. I'd simply tell those important to me that I'd be heading out to Maine one summer day (because I'd totally do it north-to-south) and that I'd keep in touch as much as I could over the next 6 months. Along the way, I'd rig up some sort of crank power charger & take copious notes on a lightweight but rugged laptop. I think I'm a talented enough writer that people would want to read about it - and if I got enough to read, maybe I could sell some advertising on the site & actually make a few bucks. Maybe somebody would be interested in "dead-tree" publishing & I'd make a few more bucks. The more I think about it, though, the more distracted I get by it - the more I want to do it. Obviously, though, I'm not in a position where I can do it right now.

However, it's been done before - there are great books about hiking the Appalachian Trail, and while I'm sure it'd be beautiful, my interactions with others would be limited. In other words, I'm sure I'd enjoy thru-hiking the AT, but I think I could do better.

Then I start thinking about my interactions with people on Twitter/Facebook, how I really want to see every baseball stadium, and Three Men in a Boat.

Start in Miami at the beginning of the season with a bike loaded with gear & go. Tweet/blog as I go about. If a friendly follower happens to ping me, stop by. If they offer food/beer/lodging, take them up on it. If they offer tickets to a game (major or minor league), REALLY take them up on it. If nobody is around, pitch a tent (hehehe) someplace safe, cook myself some dinner, & call it a night. Bike around, take pictures, write about it, get to see the country, get to know some people - this is right up my alley.

Now, will this happen? I don't know (but the fact that I'm writing about it makes it more real than just a "think I'm thinking about"). This isn't something that would happen anytime in the near future -- kids need to be more grown up and I'd need a LOT more money in the bank to be able to pull this off. Maybe a few years from now, maybe I'll convince one or both of my kids to take a year between high school & college to do this with me. Maybe this will be a "got both kids through college" present to myself (but, geez, I'm looking WAY ahead -- if I were planning this 18 years ago, the concept of "tweeting to find a place to stay" would have had me scratching my head -- let's suffice to say that I'll intend to use whatever the media-norm is to post my progress whenever I move ahead with this harebrained plan).

What say you, commentariat? Something feasible? If work/obligations weren't stopping you, what "big thing" would you do?