You have some of the best questions I’ve seen. These questions not only inform, but have a classroom type instruction base to them. Like this question here.
First off, I am not associated with the Affiliates (Minor/MLB), but it is my understanding that unless a player has negotiated differently, he can ride the winds either way as many times as the MLB club that he’s with, says so.
As far as a position player changing positions, again, if the player has negotiated differently, his direction up-n-down depends on the club he’s with. Some ride this trip for their entire career.
I know this may not seem like a glamorous life, but some make a fairly decent living – even into the coaching ranks, scouting, marketing and promotions, etc. In fact, the experience and learning curve for a man who has a reasonable personality, everyone seems to like the man, he’s accepted the route and seems to be an “organization type guy”, can view this kind of up-n-down trip as exposure to the entire organization’s way of doing business. So, as age and newer talent starts to squeeze out those with lessor ability, having someone think of a man in terms of … “how about a job doing…… “ isn’t all that bad, especially when baseball is all a man knows. It’s not a bad life, although it can be a stretch at times – especially if a man has a family.