annb9, congrats! Great choices! I love Italy, I have to go at least once a year!
Here are my tips –
When choosing accommodations, check that they not only have AC, but that they have GOOD AC, it will be hot!
If you opt for apartment or b&b stays be aware that many do not have lifts, so check into that specifically so there are no surprises.
Since airbnb has been mentioned I will point out that while it does offer some nice properties at good prices it can sometimes be more trouble than it’s worth when only staying for a short time.
You will have to arrange a set meeting time & point to check in and out. You won’t have support staff to answer questions, call a cab, book a tour or make a dinner reservation for you. Which is all fine, many people get on just fine without that, including me. BUT, only if I am staying for at least 4 or more nights. Otherwise just the check-in process alone is not worth the hassle. As well if staying for say, a whole week in one place then I am afforded the time it takes to figure things out myself. On a 3 night (which equals 2 days) stay I don’t want to lose a half hour to finding the closest taxi rank & trying to make dinner reservations.
If you’re planning on 5 bases in fifteen days that equals 2 to 3 days in each location. If it were me I would use hotels in that case. I might as well add that I would not do more than 4 bases in 15 days (I would eliminate the AC because it is most out of the way and you will get the seaside fix while in Como) You will lose a half day (at least) each time you move to a different location.
I should also add that I am not the type that likes to be on a very scheduled vacation, I do not like my whole day pre-planned or on a rigid schedule. I like to see where the day takes me. Plenty of people do like to have all or most of their time all planned out. Those types can make dinner reservations before even arriving in Italy, and having to meet the apartment owner at the cafe on the corner of such & such at exactly 3pm won’t be a burden. So if you’re that type then maybe airbnb is okay for short stays.
It sounds to me that you guys might really enjoy an agiturismo stay for part of your trip, maybe in Tuscany. I stayed in one a few years ago and loved it.
You’re going at a very busy time of year, the best & most affordable accommodations fill up fast so the sooner you can get them arranged the better.