Once converted to a rental, repairs and improvements may qualify as deductible expenses, but pre-conversion repairs typically do not.

Twenty of the the homes were BRRRR and two were full conversions from single-family to assisted living. 

Home insurance would cover anything on premise, but as @Jonathan Bock stated, it's usually for significant damage.This might be something you would tackle on your own, but worth to have a conversation with your provider first to see what they have to say.

Without getting into the weeds of our conversation, their response was as expected highlighting their service and ability to facilitate a loan.

But THANK you for you information and hope to continue the conversation.  

Quote from @Mohsin Ali: Hi all, I'm joining this conversation late. 

and it ended in a circular conversation to nowhere.

Cash for keys is probably not effective since they don't have anywhere to go [most LL are not likely to rent to them] however, I plan to have that conversation and offer any assistance with moving.Thanks again

I'd love to get more conversation going about the new MA ADU law going into effect Feb. 2nd.

I have talked to tons of investors recently and everyone says the Zillows interface is the worst, but it is just a side comment and we keep going on to the next conversation.