SS models will look much better after 1-2 years of wear compared to the Sport models. The 42mm watch for example: a Sport model is $400 right now and by the time 2nd Gen gets here, resale will be around $200-$250 and this is in a "worn" condition with scratches in both the display and the aluminum body. "Mint" will probably be $300 at best for the Sport. Now with the SS, we will all see tiny scratches on the watch which I don't think will cause any decrease in value and lets all agree that the sapphire display isn't getting scratched by 99% of users. Today with a sport band it'll cost $600 and will probably sell for somewhere around $400-$500. With the higher bands it will probably be a slightly larger loss. I think the sapphire will be the true factor for the SS because I don't care what kind of watch it is, if the sport models have scratched up displays I couldn't imagine anyone paying much more than half price especially with a new model on the way.
Just my .02