It was a legal 3-plex at the time we closed on it & there were 14 ancient permits still outstanding.

I will say that I have a few houses in HOAs and the accounting methodology they use is a bit bizarre.

The danger in using your own personal standards when rehabbing is that you may have higher standards than others in the neighborhood, and you'll end up spending money on the rehab that doesn't pay for itself.One thing I've heard around the campfire is that appraisers have different methodologies in different farm areas. 

Guessing ancient and thus increased maintenance

Hi all - my name is Jonathan and I purchased my first home earlier this year and have rented out the spare bedroom ever since I moved in.I work in commercial banking, mostly dealing with C&I and some CRE so over the years, I've picked up on some of the relevant topics, acronyms, and methodologies like IRR, NPV, LTV, cap rates, appraisals, etc.

It includes, among other things, a comprehensive map of the Cleveland area, grading each area from A+ down to F, using a consistent, objective and transparent methodology using publicly available data rather than a broad-brush subjective approach.

Unless these are d class apartments or an ancient building the repairs should be almost nothing per year.

If I'm going to get a cash out mortgage or HELOC (BRRRR methodology) in the future once the house is fixed up, should I ask for Florida form 9 endorsement fro the title insurance company now? 

This defect could be something as simple as a measurement error in the survey, to a more serious claim (ancient native burial ground). 

When you finally get to the point of the non-renewal, hopefully you will have all your ducks in a row - violations are ancient history, rent is up to date, notifications of non-renewal were appropriately made.As a last point, I think you made a mistake by informing the tenant you were not going to renew after the first month.