The only issue here is that I assume his next team (assuming he‘s not good enough for Chelsea) will prefer a 5 year contract and 100k over that term is “only” 26M. The player would be taking a paycut in guaranteed dollars if he moves in the first 3.5 years.The length of the contract doesn’t actually make it any bigger of a gamble.
The risk with any transfer is getting rid, and the only real obstacle for that in todays PL is wages.
His wages are £100k/week - an amount Nottingham Forest are currently paying - means that anyone in the PL can afford them.
So yeah, theoretically you’re committing to paying him £44m in wages, but if it really goes bad and he’s not good enough, as long as someone can afford to pay him the same, the player will choose to leave and play football rather than sit on the bench until he’s 31.
Maybe it’s worth it for playing time as you say, but then again maybe not, no idea.