All 2 strokes are to be considered high maintenence really.
I find some of the fun of owning them is taking them apart and putting them back together again.
Maybe going down the 4 stroke path would be more suitable to start with.
There were a few 250 4 stroke race reps made in japan like the cbr250 and the zxr250 (i hear they even used to bolt little turbos to the zxr) might be worth a look at them.