The two pre-IV sigs that really stood out to me personally were the 2K4s and ZK1s. Both of those are still among the best performing bball shoes I've ever played in, and I still rock my Black/Maize Is every now and then. Though they're pretty beat up now, they still feel very comfortable.
The 2K5s were ok but not really a step up from the 2K4s IMO. The IIs were a step down for me performance wise, and I generally don't like it when a sig does the whole multiple versions thing. To me, if you're gonna make a sig shoe, just make one damn shoe. I will say the Orca IIs looked very cool and were my favorite. IIIs were an awesome performance shoe, but I just never totally got into the waffle cone look so I only got the all black colorway with the white swoosh.
I will say though that aside from the 2K4s and ZK1s, I've sold most of my 2K5s, IIs, and IIIs since the IVs-VIs released, which really did change the game for the line. I now only own 1 pair each of the 2K5s (white/purple/gold laser), IIs (Orcas), IIIs (Black/White), and VIIs (YOTDs) since they're my least favorite sig models of the line, but I have several pairs each of the 2K4s, Is, IV-VIs, and will probably add the VIIIs to that list this year.