I'm planning an August 1st southbound, so a lot of these considerations about hiking with a group, etc., aren't as much of an issue.
There is pretty much no way I'd ever drop $80 for a motel room by myself. It's just completely out of the question, I'd quit the trail before doing something like that. I'm going to hike, not spend 8 days worth of trail food for a couple hours in a bed and a shower. I'm not saying that it's a bad thing to do or judging others, but I'm a 24 year old on a limited budget and luxuries like that are not the point of me doing this.
I'm not saying I'm some sort of ascetic who can live off rice and raisins the whole trip, and I will definitely give in to the occasional beer and pizza, but overall I can't imagine spending much time or money in towns, partially due to the fact that as a late starting southbounder, there won't be anything to do or anyone to hang out with.
I stated it in my OP but I'll post it again, I plan on bringing $4,000 and I'd like to only use $2000 of it.
Also, I've been a bike commuter for the past 6 years, so I'm pretty used to eating a large amount of calories in order to have the energy to get to and from work/school/wherever, and I still only spend about $300 a month eating out a few times a week.
The next question I have is the cost of mail drops vs buying crap at supermarkets. I have a great local supermarket here with many bulk items that I can buy in hiker quantities, bag up, and ship to post offices along the trail. At this point though, I'm planning only maybe 4 mail drops at certain points and resupplying along the trail the rest of the time. This seems to be a cheaper route, as doing 25 mail drops x $10 shipping (guess) = $250 in just shipping charges. Am I really going to save $250+ by not buying the same food at local mountain grocery stores and crap? It's hard to imagine the prices being that much more expensive to make the mail drops worth it.
If this gives any sort of a perspective on my mindset and preparations for the trail, I've been living off of $600 a month and saving $1000+ (over 60% of my income) since I started planning for the trip. I come from a less than rich background and I basically already live like a thru-hiker (once a week shower, etc.) so maybe some people just have a bigger lifestyle adjustment. I've been working kind of random jobs and living in random places for a while, including travel around the country as a bike rickshaw (bike taxi, pedicab, whatever you want to call it) pilot, sleeping in a tent and working days pulling fat rednecks up hills at NASCAR events and crap. I don't think the trail will be easy, but I can't see me needing to eat more than I did doing 60 miles of biking a day with 500 pounds of fat redneck dragging me down.