With one phone. With the HTC he got, there may be better hardware compatibility with the OS, which would be friggin' amazing.
But you have to realize I'm been working with mobile phones for years. I've seen multiple iterations of WinMo come and go, and I've seen all the problems the new versions have.
Trust me when I say I know what I'm talking about, and WinMo is a heaping pile of crap more times than not.