I do completely agree that if you're gonna buy a new setup, you can get a duron or tbird rig for pennies more and a whole order of magnitude more speed, but I suppose if you're really nostalgic, you might want a k6. Hell, I just bought one of the old cyrix m1 cpus just cause I felt like reliving happier days. jic tho
1. Think a socket 370 HSF will fit on a socket 7. A lot of socket A hsfs look like they'd fit too. I'd go with maybe an alpha pal6035 as you're not gonna be dissipatin a whole mess of heat and you should have a LOT of ceiling space with that thing. A volcano II would accomplish the same, but be cheaper and quieter.
2. Not much, but I've always been a fan of the k6 series. But they're just not designed to OC very well. I'd get a pc-pga celeron and an i815 or apollo 133a board if you didn't want to buy some of the OC boards for the socketA. The 65 dollar boards are virtually Overclocking-proof.
3. If you want to OC with a duron or a tbird, I(emphasis) would go with an iwill kk266+, an asus a7v133, or an abit kt7a as the kt133a chipset has had a bit of time to mature and it'll be easier to start up OCin. (This is for OC-ability, not necessarily performance)
Finally, I don't really like the concept of the kt266 as it reminds me way too much of the kt133. They slapped an "a" at the end of it and it becomes a great chipset. Hehe...maybe it's a conspiracy, only chipsets that get an "a" at the end are good. lol