Mike,
You're gonna have to have some degree of expertise in writing estimates and this is, in fact, the computer age. Xactimate, Simsol, MS/B, et al, all have training discs (I think) and if you're dedicated and can find someone to look over YOUR shoulder, you can become competent fairly quickly.
I think the secret to becoming competent in computer estimating is to actually do the estimate with someone with experience supervises your work. If you watch them, it doesn't seem to work as well. Accurate and thorough scope notes are the secret.
Assuming, of course, that you are dedicated, like 18-20 hour days, like 7 day work weeks, like dealing with folks that do not trust you, like doing your claims 3 or 4 times, sometimes, to satisfy a supervisor or manager, and the list goes on and on and .........
If you're a contractor, why don't you do the inspections and let the experienced older, fat guy do the computer stuff? Ever thought of that?