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

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

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. 

I have been renting my townhome up in Issaquah, WA for the last 10 years with no issues.

One property is free per email address if you just wanted to try it out. 

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.

Not an eligibility issue so much as who is able to take it on.  

In conducting a background check, I learn the applicant's current neighbors hate him, he's on a first name basis with the local police or he has a variety of other social/criminal issues chasing him.4.

Your property sounds to be more unique, therefor likely making it challenging to find acceptable comps. if the property is common for the area, it's likely this could be a non-issue with the right lender.