If you are doing it yourself this isn't a bit issue. 

One month ago I made an inspection and tenant stated that there are no drain issues.

But I'd sell the rentals one at a time as there are issues, vacancies, capex, etc.

The majority of the country? 

While a mini storage, apartment building or some other type may sound great they all come with their own issues and stresses. 

We have had some issues with getting insurance for the Florida properties in the LLC and also related issue with the Mortgage (which is in our name).When our lawyer requested EINs for the LLCs we were informed by the IRS that we need to file a 1065 for each of the LLCs.Our structure is that the LLCs are owned by the two Trusts (50%) in each of our names.

I’m having issues with people being able to fill out applications on Zillow.

I thought maybe she’d like the increased income and reduced liability as she approaches 90 years old but I see the tax issues might be too big an obstacle as she does seem pretty well off. 

The issue is once I pay Obligo then they aren't in the middle of things anymore.

House hacking is the perfect way to get experience in investing in real estate while also covering a majority of your living expenses.