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I've sort of taken a similar route in my computer purchases. I bought a top of the line titanium powerbook (2003ish) that can't even handle Leopard today. After buying that machine and quickly running out of disk space and then having significantly faster laptops (that could also use more RAM) come out not too long after I changed my stance. Now I don't go for the top of the line. I spend less and upgrade more often (without guilt). Now my needs and processing aren't as great as yours so it may not make sense for you.You know, I've been thinking from a cost-benefit standpoint, if I wait for the hot new machines I could probably then pick up a quad 2.66 MacPro for a song (well under $2000), and live quite happily with it for a few years. Hmmmmmmm.....
If you go with the FW800 check out Granite Digital repeater hubs and cables.With external storage, USB is convenient but it's no barn burner - and it hits the CPU for each transaction. If you have 1394 (either S400 or S800) port you can use, go that route or eSATA if you have it.