Jay pretty much covered it. You can't plan in advance for hotels at all, until the day of. You'll never know where you'll be at the end of the day. If we have internet in the car, we'll reserve a room with hotels.com as soon as we have an idea of which town we'll be nearest to at the end of the day (usually as soon as the chase is over). You can usually save a lot of money that way and avoid the ritual of driving around towns at 2 and 3 AM trying to find a hotel with rooms. Many GPS programs have the hotel phone numbers listed, you can call ahead and reserve a room that way too.
Wifi is a big priority too. Usually someone in our group has cellular internet, so if we absolutely can't find wifi, we can at least get some data for the morning forecast on their laptop.
Our worst 'booked hotels' experience was after May 22, 2004 in Nebraska - our group ended up finally finding in a small hotel in Yates Center, Kansas at 4AM, after nearly 5 hours of searching for a hotel starting in northern KS. KU and KSU graduations were that weekend and every hotel within 150 miles of Lawrence-Topeka-Manhattan was booked.