I dress Koda and Kammie probably 3-4 days a week in the summer. Of course on the super hot and humid days they go nekkid
In the winter daily due to they get cold so easily and shiver not having an undercoat.
PJ's are occasional as I don't have very many
I don't have problems with Kammie's hair, but Koda has a cotton coat which mats super easy. I found that clothes that are silk lined really help to prevent matting. Or just keep him in a puppy cut and that works too
We have never experienced any skin problems