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

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

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

@J Lyftogtin out area you're going to be in a condo that's a 1/1 or mobile type investment.

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

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.

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.

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

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.