Perhaps being a little ambitious here, but it's always good to have a general itinerary. . . I'm travelling with 3 guys, planning to stay in motels along the way and away from big meals (i.e. cooler in the trunk) and we should be put up by friends 6 of the 27 days. . . i tend to be type A in terms of planning but the road/unknown quickly does away with that. The cities we plan to stop at en route are in ( )

Jacksonville (Daytona/St. Augustine)
Mobile (Panama City)
New Orleans (Biloxi-Gulfport) - 2 nights
Houston (Baton Rouge)
Dallas - 2 nights
Oklahoma City - 2 nights
Santa Fe
Boulder (Colorado Springs/Denver) - 2 nights
Cheyenne (Ft. Collins) (Kearney, NE - why not go to NE when it's 50 miles?!)
Salt Lake City
at this point, we have 5 more days and will have to make a decision
probably based on Northern Cal wildfires at that moment:

Scenario 1) Southern route

Phoenix (Death Valley/Sedona)
San Diego (Joshua Tree/Palm Springs)

Scenario 2) Northern route

Reno (Winnemucca)
Carson City
San Fran (Yosemite/Oakland) - 2 nights
LA (Monterey/Santa Barbara) - 3 nights

Then I'm staying in LA, and my buddies are flying back. . . any advice? places to avoid, better ones along the route - I know that it's indirect, that's sort of the point, but we're trying to be efficient about it - did point-to-point distances, and the trip will be a little over 5000 miles (not too much gas for 4 people), also estimated/day:

25 - accommodations
20 - food
20 - entertainment

so 65 a day + gas - feasible??

thanks for reading!