I just upgraded my unit from HDS-8 Gen 1 to HDS-8 Gen 2.  I've been told the LSS-1 and LSS-2 box is exactly the same and that all I needed to do was upgrade my LSS transducer to the new one.  Wondering if I will see that much of a difference?  I can get the LSS-2 ducer for $250 and figured I could probably ebay my LSS-1 ducer for $100, so is it worth the $150 investment?

Yes!

The LSS-1 box and LSS-2 box are not exactly the same. With both an LSS-2 box and ducer, you would get an increase in both clarity and range. With just the LSS-2 ducer (keeping your LSS-1 box), you would only get an increase in range but not clarity.