Most of the newer PC games are multiplayable "online" - so I'm sure you could play together, but it would be quite as simple as popping quarters in and hitting "start"
You'll have to create online accounts (easy), buy two copies of the game (with the deals lately, it should be less than $20 a game for two copies).
But as badmouth pointed out, hardware (PC, wheel, sound, etc) is going to cost you a lot.
There has been A LOT of interest from friends and family with my cabinet as I've been building it. They all want to come and play - so I may end up building a second, depending on time / money / interest. I'd bet it would be $1600+ to build another from scratch, including the PC.
I know some guys spend waaaaaaaaay more than that on just an upright MAME cabinet. (and especially more on the virtual pinball cabinets)