I will answer your questions based on my own experience only. When I started losing my hair, I asked my husband to shave the rest of it off. Yes, it was shocking--but we got over it. I usually would just wash my bald head with soap in the shower. Now I have about 2/3" fuzz and I use my usual shampoo.
Many nights I had trouble sleeping, and would find more relief in getting up and sleeping in a recliner, rather than in bed. There are many websites (headcovers.com, ie) where you can buy soft chemo caps for sleeping. (They are also easy to make, if you sew.)
I can't advise you on a breast infection but I'd ask my doc if it would be ok to use an ice pack to help control the swelling and how long it would last.
Good luck. You can do this--many of us have done it, too. :-)