Welcome Taxman: The following is a post that put up several weeks ago. I think it is pertinent to your situation.
I know where you are. I wore a "system" for 23 years from age 20 to 43. I was a slave to it. I know your fear. I was very scared and worried about what everyone would say. I was sure THEY would be shocked when I shaved it clean.
Turns out, I WAS THE ONE WHO WAS SHOCKED.
I was shocked to learn that I had not been fooling anyone with my "system".
I was shocked to learn that most everyone had wanted me to get rid of it for years.
I was shocked to learn that no one cared that I did not have hair.
I was shocked to learn that I felt better about myself once I got rid of the "system."
I was shocked to learn that my self confidence shot straight through the roof.
I was shocked to learn that my hair, or the lack thereof, did not define me.
I was shocked to learn that I was happier without it.
I also had a huge plan of losing the system, getting a tan on vacation, etc. I discussed it with my wife. She was on board. I talked to my kids - age 10 & 14. I had a plan. I was ready. Then my 10 year old said "Dad, why don't you just go Friday to the barber, cut what's left and go to work on Monday." Sounded like a great idea and that is what I did. Even took him with me.
We still laugh about my elaborate plan to go SLY and how a 10 year old was smarter dear ol' dad and had a better plan.
I realize this is a long post but want you guys to know I understand where you are. These guys on here were WONDERFUL help to me. They gave me the same advice they are giving you.
TRUST ME - JUST DO IT!!!!!!!!!!!!!!!!!!!!!
I hope these thoughts help you. Sounds like your wife is on board. She is a beautiful woman - outwardly as you have told us and inwardly because she sees your struggle and supports you. That is an amazing blessing. She is not gonna leave you because you don't have hair. She loves you because of you - not the high priced system on your head.
Lastly, there is no perfect shaped head. I think my head is perfect (it's really not) because I no longer have a rug to hide it. I also could not go swimming, ride with the sun roof open, get on a roller coaster, take my hat off at a ball game, wanted to sit with my back against the wall anytime I was in public, etc etc etc.
Trust me, I love swimming now, I love riding with the sun roof open, roller coasters still give me motion sickness

, I take my hat off at a ballgame and don't give a damn where I sit in public. Actually, I do care where I sit in public - I want to be right in the middle of the action so everyone can admire my big bald head and hear them say "I wish I looked as good as that bald guy over there having a great time!"

Sly is more than a look - it is a persona!!!!!!