take Ducati singles for instance, 250 not quite fast enough, 450 like riding a jackhammer and risk your fillings coming out and the 350,smoothest and best of the bunch, all second hand opinions by the way as I've never been rich enough.
Hurrumph!

Money has nothing to do with it, loitering in the right place at the right time has been fruitful

Duke 250 narrow case are just magic with turbine power to 9,500 and with desmo head 10,000+, smooth. Described by racers whom have been fortunate to have a shot on a good Manx as a miniture version. 250 widecase bit heavier and not as nimble, the 239 French tax evasion model was better, with bigger carby and better cam. Duke 350 widecase with valve spring or desmo head goes well and is smooth if put together right, again, revs are not a problem. The 450 (436cc) is a softer bit of kit, yet will still go to 7,500 on occaision. Only a jack hammer if you rev the nuts off it through the gears and haven't built it right.
Main problem with all Duke singles is getting them to breath, the inlet size, shape and position in the head is s***e

Only cure is to fill the head with weld and re-cut the inlet port with a steeper angle and central position, then work out where the carb goes!

As for boring and stroking a 450 to ~500cc

you pays your money and makes a choice

Now that is expensive!
A reputable Duke single race motor with all the right bits, starts at £5K just for the labour

Same again for the bits (6 speed box) and same again for the lightweight chassis + carbon fibre fairing if you are lush as an extra.
Racing never was cheap!

Support those that do, if you can and enjoy.

Alternatively buy a 'Condom' 350 and take it easy!

Now that crankshaft..........? Bill