If you have a good drill sharpening situation, it almost doesn't matter where the drills themselves come from.
I second the 135º Cobalt HF bits. Very nice to not have to drill a center in the hole.
Drill grinding machines are a very nice idea, but if you want truly good results–from most machines–over a versatile range of sizes (.0625 to .500 or more) you need to learn how to do what you're doing AND spend good money on the grinder.
You really get what you pay for in terms of aftermarket service, spare parts, customer support, reliability, versatility and apparent cost/value. And I'd say you should think of paying more than $1500 if you want to even begin to get the whole kit and caboodle for a good piece of machinery.
If you can't shell out that kind of money, in my experience, you should take a week off, build the best jig/contraption you can find/dream up, and practice. Anything else is just a waste of money, but an even BIGGER waste of TIME.