For example, here is a place I stayed in while in the Dolomites...Hotel Kronblick.
Not bad for about US$64 per person which includes a big breakfast and full course dinner...
I've stayed in many just or nearly as nice that were cheaper. A room with breakfast per person ran me between €20 and €33 last summer; with dinner up to €44 per person.
The staying put in one location for a couple of days or more is the way to go. It enables you to explore the area as already mentioned. BTW, I've never booked any accomodations ahead of time. I travel in June so room availability is never a problem. Maybe others can chime in as to room availability in late July to the end of August which is when most of Europe goes on vacation.
From time to time, I might daisy chain my stops on a daily basis, but I usually stop by mid afternoon, drop my luggage off in my room, take a break and then go for another late afternoon ride into the early evening. Europeans usually have dinner much later, especially in Italy where you shouldn't expect to get served till 19:30 hours.
Microsoft AutoRoute is worth it for the ~$40. As for planning, I do mine the night before over dinner by browsing over my map.
Tip: having toured my first 10 years on an old R65 with narrow European bars and the last 4 years on a GS, I can highly recommend any dual sport for Alps touring. You want an upright seating position with wide handlbars.