Well... once K0000nah GOES NATIONAL, BAAAAYBE...
Howie will milk it as long as possible. However, does he lose credibility as he spends more and more of his time in Florida and less time as a MA resident? Right now he has an easy gig so there's no compelling reason to give it up, but eventually people do (e.g. Savage)
What happens to Grace when Howie hangs it up? She's riding his coattails at the moment but in terms of political discussion/analysis she's completely vacuous. She might be a nice enough lady and 'not guilty', but she doesn't bring the experience/resume one would expect for political talk radio.
I suppose that depends on his education. There is an unholy alliance between the media and politicians, for instance, so political consultant is always a possibility. Marketing/communication is another. I suppose those gigs aren't necessarily going to pay the same as what he was/is making (I have no idea what "the talent" in positions like VB has make) but one does what one needs to do to put food on the table.
I imagine the Albany area, from what I recollect the few times I've been out that way, is a nicer area than the Boston area is, in terms of raising kids.