Ditto what others have said - you have a lot going on. Don't be to hard on yourself.

As far as the cycling stuff - I'd hit goodwill or a thrift store. You can get long sleeved wool sweaters which will work really well for your top (maybe pick up a wicking base layer at a discount store). No rule says you have to wear tights over your shorts. There are people who wear sweatpants (even though they are cotton usually) with no ill effects.

What kind of winter temps are you dealing with?