Tch - I sure can help you with that. I spent a good bit of time figuring that out myself.
Well, what "current equipment" do you have?
Those carbide bits you linked to are the same as what I order from the guy. Call and talk to him - very knowledgeable and helpful.
The bits are all 1/8" shaft with the ring you see just being a holder with the size marked on it. That makes it easy to tell the size. Note how the cutting part is a LOT smaller than the shank? These will chuck up in anything that will hold an 1/8" drill bit.
I like a mix of them - small bits for drilling vias that only need a small wire past thru and for leaded stuff like resistors and what not.
A small 1/8 watt resistor, cap etc will have lead size around .020" so a #73/74 bit would be just right.
A 1N4007 diode has a .030" lead. I use a #68 most - it works good for DIP sockets as well as the large lead items.... and will work for the 1N4001 thru 7 series diodes.
"IF" you have a pretty good selection of HSS bits, those can be pressed into service for just one or two large diameter holes... 1/16" or 1/8" that sometimes you might need for mounting, etc.
I use the #68 most - and have a few #65 but found I didn't use them much. I'm getting ready to place another order and I guess I'll wind up with #74 and #68 as the two I will order the 10 pack of. I also need a few #58 (.042") and #52 (.063") for rivets. Most likely I'll just order a 5 pack of those because they don't break as bad as those really tiny bits.
Be sure to have the PCB very flat on the press so it doesn't rock or move - those .031" bits break at nothing.
Have fun,
Ken H>