Lots of people move as soon as the kids are out of the house. 

To not charge for it is to cover a cost that any tenant for the entire yard would need to address themselves...from the tenant side they can say that including it reduces their useable area below their 3 Ac gross...neither is right or wrong, it's just differing perspectives on what is best for them. 

He’s over cautious, so I’d like to see what sort of language is there there regarding the deed of trust.

My plan for this year is to remodel and upgrade the house to then put it to cashflow either via short/long term rental.

This is what the assessed tax value will reset to after you purchase.  

There is a reason why I buy properties that cost a multiple of what typical cheap rental properties are going for.

What will happen if she is late with rent or loses her job and can't pay rent for a few months?

It is great to see what your company is doing in the Milwaukee market!

That being said, I don't know if what I've seen is "hate."

Fast forward to the beginning of 2024- we started using Furnished finder and renting out nearly half the house on 30-90 day increments and were fully licensed as a short term rental.