Happy to chat about my experience there or send some resources that might be helpful.

Because of his experience, he knows plenty of people that he has worked with in the past that I would hire to renovate.

I think a short-term fix-and-flip loan would serve you better because, first, the credit requirements are typically lower than a DSCR loan's credit requirements, and fix-and-flip loans will fund a portion of the purchase price as well as some or all of the rehab costs (usually through the draw process).Right now, saving your cash, rebuilding your credit, and finding both a partner (ideally with a higher credit score AND experience) and lender you're comfortable with should be your priorities.

Can someone with experience and knowledge regarding this city please comment and give feedback to evaluate this opportunity?

Little money but he has a great time and makes the most of experiences. 

This gesture can reinforce goodwill and potentially secure her tenancy for longer, which is invaluable.Alternatively, if the budget allows, you might consider replacing them yourself.

Students still come despite remote classes because it is an experience.

House hacking will also give you some personal "property management" experience.

Advise is to get in contact with a lender that has experience in structuring these mortgages where you can move on to the next one and plan ahead.

Since you are a casual landlord who never intended to originally become a landlord and because you only have a couple units you're never going to get enough experience to become proficient and therefore are more likely to experience negative tenant situations. 2.