You can check backwards compatibility at http://www.us.playstation.com/Support/CompatibleStatus
60GB - limited availability, price somewhere near $400-$500, 99% backwards compatibility (I've heard), built in Wi-Fi, 4 USB slots, SD and CF memory slots
80GB - $500 bundled w/ Motorstorm, 85% backwards compatibility (I've heard), built in Wi-Fi, 4 USB slots (not sure), not sure about other memory slots
40B - $400, no backwards compatibility, built in Wi-Fi, 2 USB slots (not sure), not sure about other memory slots as well
20GB - (I'm not sure if you can find this anymore), 99% backwards compatibility (like 60GB), 2 USB slots, no memory slots, no Wi-Fi (you need an Ethernet cable to play online)
If you've got a PS2 and it still works, there's not much reason to go with the 80GB instead of the 40GB except for Motorstorm (if you like it), and a couple of extra USB slots. The memory is upgradable anyway.
If you don't have a PS2 or if it's broken, and you still want to play PS2/PS1 games, get the 60GB if you can, or the 80GB if you can't find the 60GB.
If the memory slots are important to you, then I believe your only option is the 60GB, although I might be wrong.
*Note: I went with the 60GB version before the price drop, and I don't regret the $600+ I spent at all.
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