Once your eligibility is used up you either have to stop playing or transfer to another institution that is not governed by the NCAA.
Son's roomate has two years of redshirt. There are circumstances where it is allowed. I do believe you can be granted a regular redshirt and a medical, as long as one has not played. I do believe that in certain circumstances 2 medical redshirts can be granted.
This is not normal.
Straying from the topic. I am happy to hear that Newcomers son has a renewed interest in playing college baseball!
Newcomer,
It is important that you understand the process and have all the facts on redshirted players. It is not always given for player development. One has to do their homework, watch fall and spring rosters. I see no problem with a player sitting out a year, because he truely needs to develop (I see this alot in pitchers), not because the coach asked too many to attend.