Those print servers are awful. Ugh. Also, we don't know what kind of printer he has. If it's a multi-funtion, there are much fewer print servers that will work with them.

I think option #1 is the way to go. Currently, my method of printer sharing is by plugging my standard USB laser printer into my Airport Extreme and putting Bonjour on all the Windows computers in the house. It doesn't work great, but hey, printers are annoying.