For my needs, well done 420HC or 440C (or even good old 1095 carbon steel) work just fine. My SAK's are pretty decent and I don't feel under-knifed when I carry them. So for me personally, I'd get two what many would consider "lesser" steel knives, rather than one "better" steel knife. Something in a slipjoint, probably a stockman configuration. For the money I get more blades, hence more edge than single blade knives. Time spent sharpening doesn't factor in because I enjoy sharpening. So in reality, a knife that requires less sharpening is not as satisfying for me.
Again, this is for me personally. I don't think there is necessarily a right or wrong answer to this question though it's an interesting one.
Just to throw a monkey wrench into the picture, two high quality blades, including S30V, and ZDP189(?) for $100-ish. Yup, both have been mentioned, I think. Native from Wal-Mart, plus the Calypso Jr. with ZDP. But, as mentioned above, you can also get cool things, like G-10, Titanium Frame locks, and other stuff for one $100-ish knife... Like a BM 710, BM 635, Spyderco Manix, Military, etc.
I vote for one knife. To me the fit and finish tends to better as the price goes up. Not always and only to a point. That said CRKT has some knives that are a great value. You know I thought this was an easy question until I started the reply and now