Machined jack cup install help, please

Help oh builders of great guitars!

I have the Glendale/Brian Poe machined jack cup and want to install it.
I certainly will have to dremel the hole on my USACG body to get it to go in as the paint lip is thick and needs to be removed.
My fear it that when I push it in to position, the force required will cause the nitro to crack near the cup hole.

Am I overcautious or is this a likely occurrence? Any step by step tips?

Nevermind guys, I found Boris' explanation of how to do it......

I use a Nicholson milled bastard file, 1 inch size, inserted like a spade bit, to clear out any paint or excess wood in the jack bore, so the machined jack cup goes in half way. I take a small handled, short shaft philips screw driver which I place inside the cup and just drive it into position, adjusting the strike point on the screwdriver handle to keep the cup dead aligned. No damage, no cracked paint, no cattywompus fit.

I think some finishes are more brittle than others. A relative new and supple nitro finish should be a piece of cake. A very old vintage guitar with very fragile old paint would take more guts than I have.

The MIM polyester and MIA polyurethane finishes seem to take this treatment with no issues, even did a '99 MIM 69 Thinline no problems. The cup's splines do not extend to near the lip, and the flanged area is basically recessed so there is no pressure on the finish itself. The only way to damage a recent finish if you deburred and relieved the bore hole is a mis-aimed hammer blow.

The only way to damage a recent finish if you deburred and relieved the bore hole is a mis-aimed hammer blow.

I'll let you know if that's the ONLY way to damage a recent finish ....:wink:
I'm quite good at finding all new ways to bust unbustable things....