These repairs are through a contracting company owned and operated by the PM. 

If you do decide to help them out and rent continues to be late simply have a talk wiht them and remind them that rent helps pay your bills and since you did them a solid ask for the same in return.  

@Michael Beirne Lower priced markets such as Baltimore are very difficult to operate in utilizing entirely 3rd party support.

I continue making the underlying mortgage payment myself (autopay) and get reimbursed from the borrowers payment.

I just started using PriceLabs (still on a free trial, will see if I continue using it).  

You hired them to evict the tenant, so they should continue representing you until the tenant is out.

They are a great financin goption if your goal is to continue to scale. 

Continuing to work on Second home for our Caretaker and Plantation manager to live in. 

I can only speak to myself personally but I've continued to invest, knowing properties may not cash flow much but I've invested in value-add so focusing on appreciation.

I will continue to work on the things you mentioned