I know quite a few riders who ride only tubulars and only ride on the streets. There's a few skills that one needs to pick up with regards to their maintenance, but it's nothing that complicated, either.
Punctured tubulars can be repaired pretty easily, though not on the side of the road. If you carry a pre-glued spare tire with you, you can fix a flat in seconds.
On the plus side, you'd never have to worry about pinch flatting anymore.
Tubular mounting and maintenance is a good skill to have for any cyclist anyway, even if it isn't as relevant as it used to be; just like being able to effectively use friction shifters.
If you have the money, I would definitely encourage you to give tubs a try.