Doug,
I have both the 50mm F1.4 and the 85mm F1.8. Both are very nice, very sharp primes and I really love them both for portrait work -- people and pets -- and, with extension tubes, for macro work. Neither works with the Canon teleconverters. But for macro work, I don't think that would help you anywhere near as much as the extension tubes.

I've shot with both the 60mm F2.8 macro and the 100mm F2.8 macro. Both are very nice lenses and very sharp especially for macro work. I shot comparison files between the 85 and the 100 macro before I purchased the 85 and what I personally liked about the 85 (and this goes for the 50 as well) was the bokeh at wider apertures. When you want that dreamy OOF background, the 50 and the 85 deliver. So, with all that said, you could get the 50 and the 85 if you feel you'd use them both equally for your work/play or you could decide which would meet most of our needs and buy that one plus the extension tubes (I have Kenko). A true macro lens is -- for me -- a luxury I can't really afford. I'm pretty happy with the macro images I get with my primes (including the 200mm F2.8L) with the extension tubes. And I can use the 50 and the 85 for portrait work when it is the right working distance for each. Keep in mind, however, that for most of my studio and event formals, I use my 17-55 F2.8 zoom and it is super sharp and more convenient when you have short camera-subject shooting distances.

My $.02.

Jim