I'm currently using an older Jayhawk, and I'm very happy with it. I've used the Gil-Mac, one of the older model Ovalmatics, and a couple of old AMF Sidewinders, and they were all fairly easy to use, but I'm still most comfortable with my Jayhawk. I do fantasize about a new mill/drill, but that's a few years away, at least.
If you look around, you might be able to find a Sidewinder fairly cheap; one place I know of basically gave theirs away, bits and all, just to get it out of the way. If you're going with a brand new machine, the new Jayhawk and Ovalmatic are very nice. I haven't heard much about the Gil-Mac lately.
drillbit