I think he'll go if he is wanted by a coach who believes in him and has a plan for him that Lachie believes in. Like most of these situations the dominoes have to fall in the right place so it won't surprise me if he stays either.
I don't know what digging in as you say would do to a player's reputation either. Would it harm it? I guess if he digs in and is playing good footy then clubs won't care.
It's been mentioned here he wants to stay because he likes the club, he was very supportive of Dean Hawkins when Dean replaced him, so maybe he just wants to stay and be a part of the club and play under Bennett. If so, sign a new contract for 2025 and 2026 for less (say, $600k over two years, or whatever helps the club recruit who we want).