Chris - not sure all your questions are answered in other posts - so here goes.
1. What type of pad are you using?
I use Meguiar's "soft-buf" and "Northern Mfg"(?) pads, which I got from
http://properautocare.com/. All are foam. You use firmer pads for "cutting", medium pads for "cleaning/polishing" soft pads for glazing/waxing. I use a Meguiar's "Ultimate Bonnet", which is a micro-fiber wipe designed to stretch over a soft pad, for buffing some products out.
2. Are you using cleaner, wax, glaze, polish?
Depends on the job to be done. The basic rule of thumb is to use the least aggressive product required to get the job done. If you're not sure, err on the gentler side. If it isn't enough, use something stronger. As you use stronger products, you will have to follow them with gentler ones to bring back a perfect shine.
My arsenal has a boatload of stuff, but these are the things that I'm using now because they work the best for me (listed from MOST aggressive to least)
1. 3M Finesse-IT II finishing compound
2. Meguiar's #9 swirl remover 2.0
3. 3m Imperial Hand Glaze, Meguiar's Show Car Glaze, Meguiar's Body Shop Professional Hand Polish. These all do pretty much the same thing. They are all a bit different, but I haven't decided which has the best effort/reward ratio.
4. Meguiar's Gold Class Liquid Wax (not great for longevity, although better than a pure carnauba, excellent shine. Has some very mild solvent cleaners)
5. Pinnacle Souveran (expensive, high-end carnauba. Gorgeous, easy to use, leaves white residue)
I also think very highly of Meguiar's Scratch-X, excellent for spot treatment of scratches.
3. What condition is your paint in?
Very good - these are fairly new cars. (Actually the M5 is almost 3 years old, but to me it feels new!) All that said, though - there are definitely pits, swirls, scratches, etc. I drive my cars and don't obsess about this stuff. But certainly no oxidation or anything like that.
4. Are you using an orbital or a regular buffer?
PC 7424 Orbital. Amateurs shouldn't use rotary buffers unless they are willing to invest in a bunch of practice on something other than a car anyone cares about. If I had the time, money and inclination I would go to the junk yard and get a few body panels to play with. Rotary buffers do the best work, but it is indeed possible to "burn through" the paint very quickly if you screw up. That damage cannot be repaired without repainting.
5. How comfortable are you with the machine?
Extremely. I trust it. BTW, I run it at top speed for cutting/swirl mark removing. I use it on about 4 for wax application and buffing.
6. What are you trying to accomplish?
I would love for my car to be swirl free. Never gonna happen, but I get a lot closer than most people on the black Porsche. The M5 has metallic paint and swirls just don't show much - so I don't spend as much time on them.
Finally, I've said it before but I'll say it again - ANY polishing you do is a repair to damage done to your paint. More of that damage is inflicted during washing and drying than at any other time.
I posted some thoughts on the drying part of this equation that has turned out to be very successful for many people:
The Perfect Drying Technique