That's a classic, for sure. Love those old '50s scoots.
Engine-wise, with gears, my personal opinion (valued highly by my children, as you can imagine.......):
LC singles and geared - WR250R/X. Good power, reliable, light, LONG service interval.
AC singles and geared - TTR250, XL250, SR400.
If you're going for a true "twist-n-go" auto single, it's really hard to go past the Piaggio Quasar drivetrain, very smooth and understressed, huge aftermarket, but the Kymco 250cc G3 drivetrains are slightly rougher in operation although they have excellent reliability and performance.
Having said all that, a Ninja twin would be cool.