Installing Mandrake with just about any hardware does go pretty smooth. There is always numerous resources for specific error codes. The internet is your one greatest resource for finding how to do what on which hardware. Google it, if you can't find it here, and you'll be just fine.
You may have to force some hardware to work. This just means you'll get it working, but it won't list the proper name (like windows will try to do), or may leave out functionality. My thought on this is, if you won't miss some miniscule added feature of a printer, don't spend days pouring over it.
Wine is a neat thing to have on your system, tho I have problems getting quite alot of Microsoft programs to run on it. If you have the resources, I'd like to mention that I prefer running a full machine emulator, like VMWare. Costly, yes, but you get full functionality, more or less like a second computer built in (fully networked as two computers, as well). Nice stuff, it is. Great for productivity testing, and it's an actual install of WindowsXP, 98, 2000, whatever you like. Not just a software emulator.