Edit: sorry for the wall-of-text, I got a bit nerdy with this discussion 
That did happened, but you need to remember that loans in Rome weren’t seen as we see them today, they weren’t merely a business transaction in our modern sense. When they involved the elite (and of course the equites and the senatorial class were a very close and linked elite) it was a matter of amicitia (yes, friendship did included financial help) and personal bond. It was a situation that interested everyone. The one who asked for the loan because he got the money for his enterprises (politics, mostly, even if Cicero did asked his wife for loans to buy “just one more” rural villa, lol, and capital was always an issue in an agrarian society) and the one who granted it because the one who asked became bounded not only regarding the specific amount borrowed but also because the “banker” was making him a favour, thus strenghtening their amicitia. And we should remember that having an important senator by one’s side opened a lot of doors (social ones, which opened a lot of business oportunities, and even more direct business oportunities in the provinces the senator was sent to govern and even state-level closer to home).
So from the perspective of the rich freedman, having his former master, a senator, asking him for money was never a burden, but a huge oportunity. And much of their wealth was even built on those connetions with a senator and the consequent business oportunities. Getting under the wing of a not so unimportant senator was always good business, and the freedmen recognized that. As I said, different perspective regarding loans, wealth and “capitalism”.
Yep, so were grave diggers and every other professional activity that had intimate contact with death (not soldiers, those had collective forms of purification), which isn’t to say they weren’t respected by society, they were just too poluted to inhabit inside the sacred frontier of the city.
This was the real issue freed gladiators had, because Roman society was especially sensitive with the necessity of having an heir, due to the importance of the cult of the dead. But we should remember that most gladiators were prisoners of war, enemy soldiers to be more precise, since children women and “weak” or “educated\skilled” men had much better prospects of having a good life. One of the freedmen of Pompey, a rather famous freedman that wrote a book defending Pompey’s memory against the treatment Sallust gave the dead enemy of Caesar, was, for example, a captured Greek (from Athens or close to that) prisoner of war, he was enslaved as a child and ended up being educated as a grammarian and living a quite comfortable life as a slave and, after that, as a freedman and famous grammar teacher (in a house previously owned by Pompey).
Enemy soldiers being given the chance to make a fortune isn’t that bad, at least not as bad as ending up in the fleet ir in the mines, or being sacrificed (yep, Druids and Germans and so on, I am looking ar you guys). It sucks but they had a very particular background for the most part. Not that I am trying to defend slavery, just trying to put the status of the former gladiators in perspective. Ancient World was profundly violent and unfair. Your MC is bound to be miserable, maybe going the Spartacus way or just try to run isn’t such a bad option (the punishment isn’t nice, but your MC is stuck in a quite shitty situation).
I am hardly sure of his plans, just remembered to drop by, but going unrealistic with the status of freed gladiators might not be a bad idea, it’s not that readers would held it against him. Historical fiction very difficult to work in a non-dark way for the audience if it is meant to be experienced as a RPG, especially for characters in quite shitty situations to begin with.
You seem to know more about gladiators’ legal status than I do, so it seems useful to ask, did that control over the freed gladiator passed from the former master to the master’s son when the master died? Because the regular freedmen’s connection with his former master’s house usually ended when the master died, it wasn’t hereditary in either side (there is some debate regarding this, but this seems the most probable scenario).
It should also be noted that the gladiator could had established a personal bond with his master. This is especially probable for the Roman world because of the lack of racial (Rome didn’t had racism) or any inferiority-kind of justification for slavery. Slavery, and the difference between a citizen, a free man, a freedman and a slave was purely based on law, with the free man being the dominus of his own life and the slave being characterized exactly as someone who wasn’t dominus of himself. Being a slave wasn’t even about having a master or the said dominus over one’s life (hence the not so few slaves without a master), it was merely about not being one’s own dominus.
So, the gladiator’s former master wouldn’t necessarily go against the gladiator’s wishes regarding his heir, not only because of the personal bond they possibly established but also because of his own reputation. Let’s just say that reputation was a big thing for Romans, and being known for negative actions was highly avoided by almost everyone whenever possible… There is a reason satire was so popular with Romans, they never missed a chance to make a joke or criticize others.