1 Shaggy certainly didn't look very cheerful, but I suppose that's because he lost his best bud.
I stayed away from the comb-over because my dad did that, and I got to see what it looked like before I started going bald. A bald patch is better.
Main problem for me with going bald just on top, is that I have to keep my remaining hair really short, or the "Bozo effect" kicks in. I don't know how Klingons pull it off, but I sure can't.

2 You can let it grow into a ponytail like a hippy or Unix sysadmin.

3 No, I can't: Married to a filipina who thinks really short hair looks "neater". She buzz cuts me one a month, whether I need it or not.

4 I completely understand your dilemma, Brett.  While the hairline hasn't receded much since my late teens, the sides grow up and out like kudzu; I call it the Dilbert Boss effect.   I have it knocked back every two or three weeks, otherwise it looks really sloppy.
The only down side is that I get mistaken for a cop very frequently.  Ever try to convince a barista not to give a first responder discount?