I am fairly certain that zoning has been amended to not allow new separate structures for living purposes - must be an attached addition. 

If you keep the Trust income and expenses separate from your personal money then should you ever be involved in a law suit your personal money would not be reachable. 

She explicitly said she's not self-managing that property, it's placed with Evolve to keep the separation intact. 

But at least by separating it you have it on your side of the table for negotiating.Here's what I'd be thinking about.1.

Not a 'cleaner than now' unit; that's subjective.Also, paying late and appliances not working properly are separate issues. 

.- what-separates-those-who-succeed-from-those-who-fail https://www.biggerpockets.com/...If that's not enough, ping me and I'll give you a whole collection of blogs and podcasts to follow.Bonus 2: 1) Read at least one hour per day every single day.2) Remember the quote by Jim Rohn "You are the average of the five people that you spend the most time with."3) Check for toilet paper before sitting down.

Also, if I'm trying to rent them out as separate units in the future, how do I divide the home into different addresses (ex 100A Main Street and 100B Main Street) and split utilities etc. with the city?

There is a crawl space where all utilities are separate (gas/electric/furnaces/water heaters).

In theory, you could continue doing this forever, but that's a separate conversation all together.

On the bottom table, the levies are separated by units.