Has anyone here done their own regear?

Just curious to see if anyone on here has done their own regear. I'm thinking of regearing soon and am considering doing it myself to save money on installation.
I'm pretty mechanically inclined and have done drivetrain work on a baja buggy (granted, it was a single speed gear box with a CVT, but it's still some sort of drivetrain experience). I have access to all the tools I'd need in a shop I work in and I might be helping my friend regear his S10 before my truck, so I'll have had some practice
So a few questions if you did it yourself:
1) Is it worth the trouble?
2) How long did it take?
3) Any particularly frustrating steps I should look out for?
4) How hard was it to properly shim the pinion gear?
5) If i have 36K miles on the truck, which install kit should I get, master or just pinion?
6) I'd like to get used gears to save money. Anyone recommend against this?
I might add more questions as i remember them...
Thanks

 

Max's wanna be overland build

 

That's gold. Thank you!

 

slight change of plans. So I'm probably just get a whole new 3rd member instead, which would still be cheaper than the cost of having someone install the gears and there's less things to mess up.
one question, do i need the optional solid spacer?

 

Need, no. Nice-have, yes. It keeps the pinion stable as opposed to a crush sleeve that will crush over time causing the preload to loosen.

If you are ordering from ECGS, it is worth the $25.