I've asked my current PM company to see if they have any contractors that could take a look

The idea is that they might be upset about the increase but will realize they are still getting a good deal when they search around and find out similar units are renting for $50-100 more than their renewal rate. 

You can get a loan for $30mm, but you need to come with $10mm equity to buy the company.  

.- the topics I search on BP appear to all be pre/mid covid, and have some recovery discussions post Irma.

100% have your tenant go through their renter's insurance as well as I would make sure the insurance company is notified that the repairs are already underway, they have received a rent discount, and you covered a placement for a hotel. 

I am looking into possibilities to remedy as well as getting quotes from other insurance companies.

Your mortgage company dictates your insurance requirements.  

That is a lot units to manage on your own though so if you want an all-in-one, you just have to set the expectations, but most property management companies will not live up to it in the Northeast.

There are so many deals that happen "off market" with better returns that searching on the MLS isn't worth the time. 

I'm trying to find a property management company in San Antonio for a property.