Where Microsoft beats Apple (Fonts)

To answer your last sentence, no and no.

Fonts are designed for 300dpi and up and are made of mathematical vectors instead of pixels, to make them look good on 72 and 96 dpi (Apple & MS) hacks like hinting and antialiasing are used by the rasterizers (software that converts mathematical vectors to pixels) in their products. They are hacks and not real solutions as there aren't any, they have the tradeof you mention. However I advice you to go for the hinting and antialiasing for small fonts on screen and leave the large ones alone as long you don't display it on some megascreen, they both will come out perfect on your printer (unless you made bad settings or use cheap fonts). Subpixel antialiasing is mostly antialiasing with the help of color while normal antialiasing is a grayscale one.

You can't really have this conversation without images.

What you describe as awful and jagged could well be the intended effect that Cleartype is supposed to deliver. It is designed to fit letters to the pixel grid, just a slightly finer pixel grid than standard windows because it makes use of subpixels horizontally.

Other people might give you advice on how to get "good" fonts without realising that what you want might be the OS X type rendering that they think is "blurry" and "unreadable".

Not if the type designer didn't sit down and spend a lot of time hinting the font face for lower point sizes.

Not many designers do.

I wondered what he meant here too. He knows the difference and in fact rails angrily against UK-English speakers because we use "subtitles" to describe both subtitles and captions.