I could see Monty taking an assistant job next season, or maybe something in the youth team, but not as a player or head coach. I actually think Monty's current job should be perfect for him, it's just that his skills and experience seem to have been squandered this season. In an ideal world, you'd have Monty constantly around the first team, both at training and on the bench for matches. He'd be a confidante for the players, and the bridge between the players and the coaching staff, allowing the head coach to be a bit more hands off and build his authority (which can be tricky for young coaches). He'd work closely with Baro to help him understand what the captaincy means at a little club like ours, and helping to inculcate the values of the club. He'd talk to the media, taking some of the press responsibilities off a coach renowned for his poor communication. And in particular, he'd spend a lot of time with the NYL/Academy teams, and even the younger groups. He'd work closely with young guys on the fringes of the first team, like Rose, Berry, Kekeris, Wales, Pearce, Glover, and Bingham, helping them to work through the frustrations of not being involved in the first team, understand what it takes to be a pro, and identifying technical, physical, and tactical weaknesses. He'd have a word well before a drinking culture could develop. He'd identify the most promising prospects from throughout the Academy structure and expose them to first team training as part of their development. And when the coaching staff changed he'd be able to provide some continuity.
In short, he'd be using his respect and popularity, his leadership, his playing experience, and his life experience to mentor players, bridge the gap between academy and first team, and support the coaching staff. At the same time, he'd be learning the coaching side of things in a less pressured environment than first team coaching, or even youth team coaching (thinking of what happened to Zwaanswijk), so that in a few years time he could move into full-time coaching, and we'd find someone else to fill the 'Head of Football and Elite Performance' job.
Liverpool used to have a coach employed in a job like that, who used it as a spring board to get into management in the Netherlands. I think it would be perfect for Monty, and it's kind of what I expected him to be doing this season. Maybe he has been doing some of those things, but it certainly looks like Okon wasn't interested in having anyone that could be perceived as a threat to his authority anywhere near the team. I imagine Monty would have been one of those involved in recruitment decisions if Okon had accepted the new model that's been talked about, so that's pretty telling. Hopefully the next coach is willing to use him better.