I haven't had trouble with printing in years- in fact, I can basically print on everything with no configuration, and people with OS X and Windows laptops seem to have lots of problems.
Aren't most Linux distributions still using CUPS, the system OS X uses under the hood?
(More on topic for the actual post here, the last couple of times I've tried to install Linux on a laptop getting wifi going has been a bit finicky, but usually so has getting things like booting into a GUI. I've attributed that less to Linux than to me trying to stick it on obsolete Apple hardware, though.)
Setting up HP WiFi printers is not seamless. In know how to do it (using hp-plugin), but things could have been packaged to work seamlessly.
That said, it really depends on what printer(s) you buy. I've had wonderful experiences with HP printers, and tend to recommend them. Brother, Konica Minolta, and Epson printers work reasonably well with some tinkering and research in my experience.
Canon? Godspeed ;)
I see a lot of recommendations for Brother printers, but they seem to require quite an involved process to set up.
Don't buy Lexmark, basically.