NES to SNES. Good as the NES was for the time, its games aged very poorly overall, while SNES games are timeless.
Master System to Genesis. Similar to the above.
Game Boy/Color to GBA. Again similar to NES to SNES.
Wii U to Switch. The difference in library and functionality is gigantic.
For me, Gamecube to Wii. Going from a great but 'samey' system with a relatively small library and a decline in the quality of many first party titles due to rushing them out in an unfinished state to a system that changed the way games are played and whose innovations are still used today, and has a library that is both larger and better than its predecessor. Even some of the best Gamecube games like RE4 and Metroid Prime were much better when rereleased on Wii.
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