I think Damar's case is a lot different than someone like Kenny's (when discussing the 4 game rule) because Damar had legitimate injuries and time missed during his true freshman year. He was injured both before and after he played and played under 3-4 games. People forget how badly he was a hurt for really over a year or two (it lingered from HS).
When utilizing the medical redshirt rule(s) and the 5-6th year, the NCAA at times, even in the distant past, has been lenient in certain cases. Damar's situation really falls into something that they would have always considered for another year of eligibility because his injury situation was persistent and likely has a ton of documentation. He also did not play many games as noted.
I would guess his situation has only a few handfuls of players around the country that can say the same. I cannot remember another Pitt player in the recent past that truly had a similar situation. Maybe Shocky but he was a lot more healthy and available than Damar was (he also played solidly more games).
Kenny, on the other hand, probably has a lot in common with a lot more guys. He was always healthy, some injuries happened, and he basically had to play later in the year/took a few nothing reps for a game or two. I doubt he really has a case to get his 5th year, unless the NCAA wants to open the doors massively.