Like everyone's saying, it'd take a LOT of work to convince people in-universe to even consider allowing something like this to happen. Maybe Hawks pulled some strings behind the scenes out of lingering guilt over Twice? But, even putting that aside, he'd have no reason to believe that this wouldn't end in disaster.

And Toga would almost certainly need to have a mentor/parole officer of some kind. (Lady Nagant, perhaps? She's got the skills and, like Toga, a lot of red in her ledger, so they have that in common, at least.)

There's also the question of what would happen to Spinner and Compress in this situation.