This will provide you two benefits:1) Help you better define the position, so you can hire a better matched person2) Make training the next person easier

Hiring unlicensed and uninsured contractors is considered  an exclusion under most property insurance policies, meaning you could be giving up that benefit as well.

I want to give them the benefit of the doubt they are just struggling with staffing but now have seen some red flags that lead me to believe there might also be some type of deceit/fraud and possible financial trouble.

If before getting a permit you have to dance around for Code Dept officials/ city gov and crime is thru the roof, investments will definitely be low whether real estate or other, but it should be benefiting the city officials to keep things that way.

Do they include energy tax benefits within their study?

Additionally I would add a benefit for you is that you're in great area to be able to invest locally and can invest in your own back yard as they say.

Many lenders allow for low-down-payment options if the rental income covers the loan.You’re approaching this deal thoughtfully, but be sure to communicate the benefits of your offers clearly to overcome resistance from the seller's representative.

I prioritize appreciation, tax benefits (rental property expenses, depreciation), ability to use leverage, and passing on generational wealth with real estate. 

They are usurping your property for the benefit of the public.

What's the benefit of the $149 sub through TurboTenant?