I think your best bet for seeing Tuscany hill towns on day trips from a base using public transport is either Florence or, better yet, Siena. It's just tough to get around to them from other locations. (We have done hill towns twice by car, which I love.)
Maybe some mix? 3-4 days in Florence or Siena, and 3-4 days along the coast somewhere.
I agree with those who say late Oct. is not going to be a great time to visit Lake Como. You might get some ok weather, if you are lucky, but you should not expect it. And, as noted, much will be closed already. I'd save that for some other time.
I think you are better off doing some city sight-seeing, like Florence, or Verona.
Italy is always good. We did Tuscany in January a few years ago, and loved it. (Timing was because our daughter was over there already for an art residency.)