I've been a developer for nearly 20 years and am now spending a majority of my time helping to educate people like you so that you can become the developers in your communities! 

-Administrative Burden: Managing substantial services may require more administrative work and potentially higher costs in terms of time and resources.Some investors do use creative strategies to maximize tax benefits, but this particular approach of converting long-term rentals into an active business reported on Schedule C while providing substantial services is less common.

Is there a number of times I repair it and then increase the rent a specific amount to cover the repair bills.

The other issue is the time and energy it takes to sort this out if you end up being reassessed (some people never have it happen.)  

Any guidance or insights you can provide would be greatly appreciated.Thank you for your time and consideration.

What strategies are others using when looking at MLS listings at this time?

While they've paid rent on time each month, the wear and tear along with the mess are too much to continue lease.

I serve on the board of the local REIA (CFRI..net) and connected to the investor community here as well as being a full time Realtor®.

I got the vibes that I was wasting their time or that I would not have the money to provide their commission. 

May not happen any time soon, but the law already exists permitting the jurisdiction ability to not allow STRs in ADU or JADU.