Hey man, my upgrade path throughout my life with my personal systems was
Pentium 75 - Pentium II 350Mhz Deschutes - Athlon XP 1700 - Athlon 64 3000+
Respective bus speeds
66mhz, 66Mhz, 266(DDR), 800(DDR HT)
I can personally say that making the jump from a 266Mhz bus to the 800 mhz bus shows a BIG difference alone. The backbone upgrade you'll be doing will hold out for quite some time. I even went the miserly route and bought a Socket 754 board, and it's been in use for about a solid year now, and it's running just fine. The videocard I have though could stand to be swapped out for a 6600 or higher, but I'll say that upgrading to Socket 939, or hell, if you're not concerned about cache and 64Bit operability, grab a nice, inexpensive Sempron chip, and stick with 754. Of course, if you go the 754 route now, you're pretty limited in motherboard choices, as they're all kinda low end. I got lucky and got a K8V SE DLX, the cute Black PCB Asus board that runs 754 chips. 939 Boards seem to be of better quality, and you can also get into the VIA K8t800 Pro chipset, if you're a VIA guy like me.
Of course though if you want to be able to upgrade for the future, make sure you're getting into a PCI-X board, I went looking for AGP cards and it's getting reallllly scary for whats available. Either you gotta shell out a ****load of dough, or you get some nerfed card that's not worth the money you spend. (at least that's how I see it.. heh)