My parents are fully supportive of this - they've sent me into worse unknowns before.
A few friends will probably be 2 to 3; these are people that I go to high school with and hang out with all the time. We've gone on trips together before to the beach and whatnot.
So 8,700 miles direct. I doubt we would venture far off that, but still I'll call it 10000 miles. We'll probably have about 60 days, so that would come out to an average of about 160 miles per day. Which is I guess between 2 and 4 hours depending on the speed of the roads we're traveling. That's not bad at all, in my opinion. Even if we stayed in one place for three or four days it would only take one or two long days to catch up (Right now we're looking to spend three days in Las Vegas, Seattle, New York, and DC and two days in a few other places.) That means that it wouldn't be very difficult to stay on schedule. And if we get down to it we can always decide to cut off part of the trip to go quicker.
Frugally for us I would expect to mean all sharing a room in the cheapest motel possible 80 to 90% of the time, with only an occasional more expensive night. Eating would be pretty basic too - some snacks and drinks from a cooler, and figure about $20 food per person per day, with a few exceptions. I know that through the South and Texas we'll probably eat breakfast and lots of lunches at Waffle Houses and diners. We'll probably get a national park pass ($50, right?) and bring a few hundred dollars each for miscellaneous attractions. Right now, living like this, we are figuring about $3000 per person. Is that analysis fairly accurate, or are we underestimating the costs?
Appreciate your help!