Well, first off, Cab's right. The private system of trolleys and streetcars was an effect movement device in the early twentieth, and late nineteenth centuries. What's more, I'm assuming, probably better maintained than our current system of transportation. The issue of maintenance is funding, right?
SO, a private system of highways (which I'm not convinced wouldn't have been built without government assistance--though it might have been built in a different fashion re: no massive destruction of housing). That said, privatizing the road system would do much to improve the problems of maintenance. A simple user fee would relieve any necessary taxes (taxes, I add that wouldn't be imposed on someone if they used a different means of moving around). Put purely: a product wouldn't be used if its all fucked up.
I think O'Toole's correct in that more sprawl would relieve SOME housing costs; and that the government shouldn't be subsidizing development in the inner city (particularly when it's subsidizing condos for the nouveau riche). I think that mass transit would work better if it was returned into private hands (like it was before); you wouldn't see too many additional trains-though bus service would probably be massively improved. For instance, there's a bus service my school uses to ferry people between its campus and downtown; at the same time, Tri-Met also runs a bus through the school, too. Practically no one uses the Tri-Met bus, and everyone who wants to get somewhere rides the Raz (Raz Transportation provides the service). It's cleaner, friendlier and speedier than the Tri-Met Bus (I speak from experience, I used to use the bus to get to my previous school).
Lastly, I think that there is no perfect example of a true free-market system in existant. Earlier models were marred by slavery, government corruption, repression of workers, etc. I, of course, don't think that the world would be worse off under a free market--but better. But, these are opinions based on the facts I've gathered so far. Above all else, I consider myself a pragmatist. I'm a Libertarian because its the most practical party (though a little too beholden to purists) for me. If ever incontraversial (I think I misspelled that) evidence is put before me, I will readily change my views. That's it.
"Δεν ελπίζω τίποτε. Δεν φοβούμαι τίποτε. Είμαι λεύτερος"