Wndows media player to Apple Itunes

I have ripped quite a few CD's to my external hardrive using WMP11 as my library. They are ripped in Windows Lossless format. I want to purchase a new computer and was thinking of switching to Apple. Would this be an easy transition. Can I hook my external to the Apple and play music off it and use the Itunes setup or would this be to complicated to do. Should I just purchase another Windows PC.
Smart Audio Converter doesn't appear to support Apple Lossless. But the one I mentioned above, dBpowerAMP Music Converter, might.
I was talking to a saleman at Comp USA and he said that the mac would be able to read the windows losslees file and that I-tunes would be able to convert it to Apple lossless. I don't know if he was being honest or just said that to make a sale.I guess I-tunes will create a music library once it reads the file.
Well, I don't have the absolute latest version of iTunes, but if it can convert WMA files to Apple Lossless, it's news to me. I'd check with a Mac list somewhere before I believed it.