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I wouldn't be surprised if he calls it a career after his current Ferrari contract is up. He's got to be around 50-ish and hasn't be missed a race or two over the past couple of years due to poor health?
Personally I just can't imagine him at McLaren and/or working under Ron Dennis and Adrian Newey. But still there is the old saying that there are no common friends in F1, only common interests.
It depends what Ross wants I suppose. Other teams would surely take him and now would be a good opportunity to sign a big money deal for another team. For if nothing else, it would be a nice little nest egg for when he does retire.
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