You should not have any problems getting either a usb or wifi printer to work with Windows. My iMac, well that is another story. Some of it was my fault, some not but in the end almost two hours to get my new HP printer / copier / scanner to work properly.
If you want to use it to it's full potential, yes. Most printers will "emulate" earlier printers. For decades, the "HP LaserJet II" was the default mode of pretty much every laser printer made. And you could use the HPLJII driver just fine, but this limited it to operating at the abilities of a LaserJet II. If your new printer had say a higher resolution, or the ability to collate or print double sided (or even in color), it would not do so until you add the correct driver. Plus most drivers available from the manufacturer are improved from the one in either Windows or even the disk it is distributed with. Myself, I never use the Windows driver or the driver that an item came with, I always go to their site and download and install the most recent driver before installing new hardware. I also about every 6 months check the drivers for all of my hardware, and update it if a newer version is available.
