Here's the new and improved plan. I've been crunching the numbers and seeing what I can afford/have time to do. I've had to streamline the trip to make it more, I dunno, efficient. Some things that were too far out of the way (such as Miami and New Orleans) had to be done away with. I still hope to go to those places, but this trip is just not the time.
I had to limit it to about 30 places, over about 75 days (avg. 2.5 days per place, but some places I'll want to stay more than that and some places less than that). This is still packing quite a bit into the trip, so I'll be pretty damned busy. Here's a list of the places that I'm planning to visit.

boston, MA
somewhere in CT
new york city + nearby jersey
philadelphia, PA
richmond, VA
raleigh, NC
asheville, NC
athens, GA
atlanta, GA
columbus, GA
nashville, TN
bowling green, KY
indianapolis, IL
chicago, IL
bloomington, IN
st. louis, MO
springfield, MO
denton, TX
fort worth/dallas, TX
austin, TX
san antonio, TX
santa fe, NM
albuquerque, NM
seattle, WA
olympia, WA
portland, OR
eugene, OR
san francisco/oakland, CA
santa barbara, CA
los angeles, CA
Traveling via Greyhounds, Megabuses, Amtrak sometimes, and flying from Albuquerque to Seattle. Transport budget is $1500, which is an average of $50 per journey (that should be about right, as the bus fares average around $25, and the trains and plane will obviously be more. Food budget: $750 (average of $10 a day, which should be a piece of cake considering that I currently eat for about $3 a day). Another $500 budgeted for "thanks for letting me stay/hang out with you, i love you" meals or drinks or whatever. Another $750 for entertainment/hopefully very rare nights of having to get a motel room/misc. Total budget: $3500. Am I forgetting anything? I should have around an additional $1000 that I don't plan on spending but can serve as some sort of emergency fund. Hoping to not have to pay for lodging by staying with friends/family/couchsurfing. I'm more likely to rough it than pay for a room.
I THINK that I've budgeted to make this comfortably affordable for me, such that there is plenty of room for error built into the budget.
I will try to set off in early October and make it home by Christmas or New Years. Much of this is still up for change, so suggestions are welcome!

