1) Assuming the outside diameter of the hose is 5/16" and the drill bit is 5/16", on a scale from 0 to 10, how likely is it that insects, vermin, or demons will get into the house in the space surrounding the hose? (If I have the OD wrong here, I'll still use the right sized driill bit.)
I can't caulk the outside for a few weeks, and iiuc it's not worth trying to caulk the inside, which has carpeting and then plywood, because even if that keeps the creepy crawlies out of my bedroom it wouldn't keep them out of the space between the outside and the inside.
2) Also, any reason why I can't drill out from the inside, rather than drilling in from the outside? Normally I would say that the first is much safer, but since the co-ax is already there, it's easy to to position the new hole from either the inside or the outisde.
As an aside, when last fall I removed the ivy I used to have growing up the front of my house, I was forced to remove the screen from the upstairs window at the front of the house (my bedroom is in the back). It's always been very diffiicult to remove or replace that screen and I couldnt' get it back in, so the window has been open about 10 inches ever since April or May and I haven't seen a single insect in the house, not even in that room. Even I don't see how this is possible, but that's how it is.