I think that Wyndtell's customer service is really improving - however - I am not advocating them
I would do very well without their service. Unfortunately I was suckered into a 2 year contract (ending this August) and so thats that. There once was a time where SK was not free or cheap, that was when I signed up for my wynd.
Anyways, what really sucks about wynd is their coverage. They claim to have full coverage in certain places, and then it doesn't. Their excuse was that weather conditions, uphill/downhill makes a difference. I don't care if I keep my pager only 10 feet away from the window, it should fking work. 
So, you want hassle free service? I hear SK is good
1 or 2, i dont think it really makes that much of a difference. I suppose it depends on what your needs are. All I wanted was mobile email, and thats still all I want. To each their own :P
edit: i realize my whole post has nothing to do with motorola =X whoops :P