Insurance was way more expensive this time—which I've heard is a nation-wide phenomenon—and it's the first time since the NAR settlement that we've purchased, so we had to cover part of our agent's compensation.

Any impending Insurance coverage or increases?

It isn't having paid off properties that offers security, there are still taxes, insurance, maintenance and management involved. 

-Will it be robust enough to track additional business expenses that are NOT tied to a single property (IE; Business insurance, Home office, ETC?)

Also, be sure to notify your insurance company that while you are still living on the property, you also have tenants. 

I would think their loan documents give them the right to control the property after the original owner dies - regardless of who is living there (although I have no direct knowledge of the laws where you live).There are details we don't know here... like if you want the house for sentimental reasons, or because you see the value between what it's worth on the market today and what the reverse mortgage company wants for it?  

Also being able to write down/document goals I set earlier and see if they are being hit.

Clouded titles are often uninsurable from a title insurance perspective. 

If so, you should also look into the insurance requirements during construction (both builder risk as well as the GC's policy, but particularly the GC policy).

I had to have an awkward conversation with my favorite realtor when their broker suggested everyone had to pay a $700 “document fee” on every sale.