Friz,
I started losing my hair at the same age and started on rogaine immediately. When propecia came out, I started on that too. My hairloss slowed down and didn't have a HT until 33 to fill up the corners only.
Looking at your pics, you're not bad. You have a good chance to accomplish results with medication. You're everdoing it with hiding your baldness because you're not bald. Quiting good paying jobs??? Are you serious?
Many balding guys get dates and couldn't care less.
I would've felt fine being bald or thinning. It just that if I could improve my appearence then why not...
I suggest if medication didn't produce any improvement in a couple of years and it's still bothering you, then consider a HT from a top notch doc and you may have to travel for that... BUT and it's a big BUT, it's highly advisable not to have a HT at a young age.
HT is a big decision. Take all the time you need doing tons of research.
Again, balding or thinning is not devastating...