It is impossible to answer the question without knowing budget, how long you want to stay in various places, etc, but with that caveat out of the way…#2 certainly doesn’t strike me as absurd. I’ve driven out west twice. Once I went north and once I went south. I did it both time in way less than 6 weeks. Of course, I didn’t stay in any one particular location for very long. I separately went out to Yosemite and Las Vegas, but I flew that time (it was my second time to Vegas).The cost of things in various places is wildly different in the US: http://www.expatistan.com/cost-of-living/country/united-states. Of course, if you want to go to places like Boston, NYC, and DC then it is worth paying the premium. The other thing about those cities is that parking can be expensive. DC and NYC have park and ride locations. I assume Boston does as well, though I haven’t used them. I’ve taken the bus to Boston before and also parked at a hotel and then used mass transit. It’s certainly doable.
If you do decide to take the southern route, you should make a stop in Mississippi and hang out with Ryno from http://rynothebearded.com. If you make it out to LA, you should be able to meet up with some people from ccmixter.org. From a music point of view, Nashville and Memphis are both worth checking out as well. There are a couple of CC musicians I know about in Nashville but I don’t know if there are the types that would be interested in meeting up with a random CC musician like Ryno or the people from ccmixter would be. Gurdonark is in Texas somewhere, and I definitely think he’d be one interested in meeting up.
On the east coast, if you go up to Maine you should be able to meet up with Mike from blocSonic.
I’m happy to give more thoughts about where CC music people are or what cities/places would be worth visiting. The drive from the east coast to LA is worth doing just to get some perspective on how massive this country is.
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