I've done at least 7 long road trips, including cross country on a bike and 2 weeks in Italy and this is always my approach. I mean if there's something you want to see put it on the list. But too much planning ahead of time is stressful and can cause more problems than it solves since it can lock you into a schedule. I find it incredibly freeing to wake up, grab breakfast and then go, "Okay, so what do you want to do today?" On many occasions we've ended up staying an extra day or two in a place because we were having so much fun.
There are hotels nearly everywhere. There are a few empty stretches out west where you may need to plan ahead a bit. But for the most part when you get sick of riding for the day just stop and get a room. You'll only have trouble finding a place last minute if you are in a super popular locations during peak season.
I've also seen a lot of bikes covered in Touratech gear, and bikes that aren't. The gear isn't as important as people think (except safety gear). Once you're on the road you'll find out pretty quick what you really need. There's a store in every city somewhere that will sell it to you.
Sounds expensive tho, how do you pay for it?