I recently saw the above ad for ZunePass, Microsoft's unlimited music service. Basically, you're renting music as opposed to buying it. I'm not against the concept of a music subscription service, I just think they could have done a better job in the ad of promoting the pros versus always comparing/contrasting with Apple. At some point, Microsoft just needs to go in another direction with its advertising strategy. Always comparing yourself to Apple is a sure fire way of constantly reminding people that a highly competent (not necessarily better in all cases) competitor exists. Same thing with the latest Laptop Hunter commercials.
So here's my free advice to Microsoft. Pitch your strengths versus the strengths of your competitor. Stick to the fact that there is more choice in hardware for PCs, they almost always cost less than Macs, Microsoft Office works much better on a PC than on a Mac, Exchange is better than whatever is available for Macs (is there anything available?), and the fact that most IT folks hate supporting Macs.
The good folks over at Penny Arcade made a very insightful and hilarious comic mocking the latest ad.