I'm planning on doing some WWOOFing this summer and rather than drive/take train/fly, I was thinking about using it as an excuse to take a nice long walk. I'm no stranger to long hikes (I worked Trails for the Park Service), but I've never backpacked outside of Parks/Forest Service/BLM lands. So I come to you looking to predict problems. I'm starting out in Florida and will end up in NC, TN, or KY. The idea is to have at least thought about most contingencies before i hit the road. Thanks!
Loc: East Texas Piney Woods
I just started reading some journals by a hiker named Nimblewill Nomad. Read his 1998 Odysey and that can give you a good idea of what to expect. Of course, the data is 10 years old but I think a lot of it is still relevant. You can also check out Trailjournals.com and find various journals through Florida, the AT, the Benton MacKaye, the Pinhoti and various other trails.
If you think you can, you can. If you think you can't, you can't. Either way, you're right.
What to look out for in Florida's urban wilderness?
Well, there's the likes of Danny Rolling, Gary Ray Bowles, Bobby Joe Long and of course Ted Bundy. But they're gone from the scene now. Unfortunately, they probably had disciples.
And Aileen Wuornos? Her body count in the Sunshine State was seven. But the good news is she killed truckers, not trekkers.
(addendum:) I'm editing this to keep the response at least a little relevant, although it pays to be careful while walking solo in an urban environment.
That long trek you've got planned sounds great. The Florida Trail would be a great way to start. Reading that book, "Planetwalker," by John Francis, who took off walking and quit speaking and riding in a car, is a great inspiration.
I plan on something similar, except I've never backpacked before and I plan on taking the subway to give myself a head start, then possibly a bus, before walking 15-20 miles to a campground (Croton Point Park) then maybe another 20 miles to Ward Pound Ridge Reservation. I'll do more research on the area I'll be walking through. All I know is it's not so good. Your hike is longer so you'd have a lot more research to do. I personally wouldn't take a chance doing it without researching the neighborhoods.
Google Maps has an option for walking directions, but it doesn't know which roads have sidewalks so you may want to zoom in on Google satellite map to look for sidewalks. I don't mind it for 20-40 miles but for something much longer I'd try finding a good route some other way.