If I have a phone with Windows 5.0, can I upgrade it to the new 6.0 when it comes out?

Answer 1

99.99% of the time, no. Because by the time the new windows mobile comes out, there is already new hardware to support it. And of course they want you to shell out the money to buy the new hardware. Ask yourself this, right now can you by Windows mobile 5 and install it on a device that natively runs Windows Mobile 2003? I think not. Not without some serious hacks that go way beyond any normal persons capabilities.