I only see memory problems under very specific circumstances. I do not sync very often, and my playlists are very static. So, for me, it would not be an issue. Plus I am very comfortable on a unix command prompt and messing with disk drives.
As for memory, that is in progress. Chips for the upgrade have been obtained, and I think it is really just a matter of time until either hijack or the player application will support it.
And before anyone asks, I am not taking orders or requests for used 80GB drives until the 100s are installed, tested and working...
As to if I will be the first, I don't know. Last time (with the 80GB drives), there were a few other folks that upgraded at the same time as I did.