I would go for the quickest route (not shortest) and make it a 1 day trip each way. I know I'm good for 600+ miles in one shot, and I'm sure I can do much more.
To the topic at hand, I havn't yet, nor will I be making a reservation, I fully plan to rely on the kindness of others to open up their hearts and rooms to me, and I will chip in on the bill. I just can't make any type of guarantee that I will definately be there until I actually get on the road.
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