I'm planning my first cross-country road trip with my best friend. I've been done with college for a couple years now and regret not doing this earlier. I drive a very reliable 2003 Corolla that has almost 100k miles on it and gets 35-40 highway mpg, and has been on several nice shorter trips without any problems, each around 1,000 miles round trip.

I need a little help from some seasoned travelers figuring out how much this could cost in time and money. For a few destinations, I have family and friends to stay with to help ease financial costs, and I'd like to spend somewhere between 2-6 days at each place. I'm also not limited to going in the summer; I may go in the fall or spring when gas is usually a bit cheaper.

So far my destinations are as follows:
Red Bank, NJ (start)
1. Charlotte, NC (have family here)
2. Kennesaw, GA (near Atlanta, have family here)
3. Little Rock, Arkansas
4. Austin, TX (have family here)
5. Albuquerque, NM
6. Boulder, CO (have a friend here)
7. somewhere between Boulder and...
8. Chicago, IL
9. Pittsburgh, PA
Back home

Does 2 months max sound reasonable? I tend to be prone to "sidequests" and distractions, but that shouldn't take away too much time.

Thanks!