It may become not worth the effort, since you will likely need to run a dormer of some sort to get more head height.  

What sort of insurance does the manager carry to make sure she can make you whole should things go wrong?

An attorney will help you work through other issues and matters, as there will be several that you guys need to sort out. 

We’re also considering purchasing another LTR near Disney to eventually enjoy with our newborn—a celebration of sorts for future family vacations.

I just sort of wing it.

Sort of looking at this as diversification of my portfolio.

If your employer was not owned by you or a family member that sort of self dealing would not be possible.

Let them sort it out.If this tenant is a problem, I would suggest not renewing their lease when it comes up for renewal.

All of the stuff he shares is already out there for free but usually when you pay for some sort of course, academy, seminar, etc...it's more about that information being all in one spot, organized, access to mentors, etc.  

I find data on free sites like Zillow extremely helpful for days on market for certain homes, and it allows you to sort by bedrooms to see how long a potential property may sit on the market at this moment (great for comping rent prices in the area as well)if I were to live in the property, I would take advantage of the FHA low down payment option to keep cash in my pocket for Reno costs  Hope this helps!