Depends on the controller and how you handle it. I had a PS2 controller clone (it was in the form of a Dualshock, but with a USB plug) that I bought for just 180 pesos back in 2010, and it fucked up after several accidental drops, adding to the fact that the wire was shoddily-connected.
I did buy another one, but it was in a somewhat different form factor, and came with a translucent casing. It seemed kinda sturdier, but I'm not sure if it'll last just as long. And yeah, PS2-to-USB adapters do work well, minus the force feedback. Contrary to what the saleslady claimed that it won't work on Windows 7, it does, albeit plug-and-play.