I'd see if it could be bored/stroked to 300+. A lot of bikes we know and love are bored versions of bigger bikes. Taking from what I know, meaning Maico, the 490 was a bored 440, which was a bored 400. They all shared the same stroke, and the rest of the engine (transmission, clutch, etc.) was virtually the same. Even the new 320 is just a bored-out 250.
Sure, you wouldn't have a 250 anymore, but that's what I would do if I had to challenge a 300 with a "250."