He doesn't have to be on crutches unless he's actually ruptured/ torn the Achilles.
A protective boot will suffice although I doubt he would be wearing one at Centre Parcs lol
Yes, he was at the Middlesbrough game sat up in the stands.
I doubt you will see him pull a red & white shirt on for the first team squad - besides options to bring Kioso & McCart back if necessary.
Personally I would pay him off but then it's not my cash that's operating the club.
Btw - I don't think he's on a Pay per Play deal - contract whilst end of season - ( stand to be corrected on that one.)