Ok now I see where you're going with it - Nightprowler had emailed me as he saw I did alot of wire work and told me what he wanted to do and asked me what kind of wire I would suggest. I suggested he try using coated leader making wire, pretty flexible, he got brown
http://www.jannsnetcraft.com/afw-leader-wire/
He moded the mold and poured them with the wire in. I was a bit worried about it with powder painting them and having to cure but it actually worked out well and he cured some at lower temps but for a longer period of time. You have to bend the wire guard up while you're tying the jig but it's not that bad. He sent me some to try the whole painting and curing process and they worked good. Here's one I did showing the wire guard
As you want to drill in - you might want to do the drill hole first and find a piece of lure making wire about the same size as whatever size guard you decide to try and insert it then powder coat and cure, then pull the wire and glue the guard in. You could try some with a wire in and some without to see what works better, and what would cause less likely hood of the paint chipping. He also has the Y-guard mold now.
Cadman one of the guys here and TU who use the bristle weed guards or Y-guards use a teflon pin when pouring the head and powdering and curing then they glue the guards in with epoxy after tying the jig.
Just a couple of different options for you, and might save you some time and headaches.