Thanks for the response as well Paul, my concerns are not necessarily around depreciation (I’m pretty sure that buildings are depreciated over 27.5 years opposed to 20 years) or other deductions that are typical to long term rentals but rather tax guidance that dictates what is a schedule E rental portfolio vs. a schedule C business similar to hotels.  

Often a decent Handyman can address virtually all or the issues in a day or two.  

So, back to my point, which you haven't addressed, other than to claim you've spent 6 months promoting "crediability" for your business rather than fine-tuning your message. 

Our only concern is a black swan / cataclysmic event that we cannot predict or have not weathered. 

I dont want to sound insensitive but it is a concern and I am hoping to get others opinions.

I am more concerned with putting myself in a position to continue to expand my portfolio.

You may want to consider liability concerns about forming an entity and the pros and cons to that.

I'd much rather have a price concession and have the buyer get the work done themselves.If you want to shoot me the address, I can tell you how many days it was on the market, vs the average for the area. 

Regardless of the fact that it likely won't be approved, it is just a bad idea if it was approved.Here are my concerns and questions: No-one ever knows if their relationship will last 30 years. and I don't want to be in a 30 year contract with a significant other.

(Note however that the notice you posted concerns violations observed in March 2017.)