Honestly, my time is worth way more than a few hundred dollars but I would absolutely confront them about the problem.

steer clear meaning don't try confronting property management?

I would not converse with tenant in any format, as things could end up in court, if he declines to leave and has to be evicted etc. also don't confront in person, you said he is MMA fighter, good rules to live by include : Never get involved in a land war in Asia , and never anger a man with Cauliflower ears.

The times I did enter into a house after barment, I did know about the history of the house and I was positive that I would occupy the house without a confrontation which made it easier.  

When I confronted the owners about the dogs he didn’t want to hear anything I had to say.

I confronted him about it twice already cordially but he gave some BS excuse saying he can see down his fence line with that cam.

Read your post about the dangers of confronting tenants in default.  

Now the platform withdrawn the previously paid rent without confronting the tenant's bank/CC... 

And negotiation doesn’t have to be confrontational, and there is an art behind it. 

It sounds like an honest mistake was made years ago and most people when confronted with this type of situation are reasonable and will sign whatever is needed to correct it.