It is important to "feel good about yourself" and I think it really helps with your recovery. I remember looking in the mirror and thinking I had been in a street fight right after surgery. So, die your hair, wear a wig, dress up...what ever it takes. I was 60 when I had my surgery, have a head full of gray and white hair, but I am a weight lifter, and muscular, and rather youthful for my age. The surgical nurses all bet on my age during the surgery...missed it by 20 years...and the doctor told me about it. It made me feel great that day. Those little things will help you through this process.
Just ask your doctor about the insurance. They all want to get paid. You are fortunate to be insured, and the docs and hospital will help. Not a big deal.
Recovery is a big deal. Everyone is different and it depends on how large your tumor is, location, surgery or radiation, age, physical condition, and lots of other things. This is going to change your life, but you will find that most people here have had good outcomes, and a few have had problems. None of your questions are stupid or silly. Good luck to you.
James