They will think you are running a tenant screening/tenant application fee collection scam. 

I pay 4000 a year in taxes for a brand new single family home I can only collect 1100 a month on....4 months of rent to just cover property taxes,  insurance is another 4000k.... that's 8 months gone.  

They collect a month of rent and then walk away, whereas a property manager has to deal with that tenant for the next year.

In particular:(1) Should I hire a law firm or collection agency to facilitate the transaction?

My goal is to leverage my hospitality background to create unique and profitable real estate opportunities.I’m here to learn from the collective wisdom of the BP community and share my experiences as I navigate this new journey.With gratitude and excitement,

This of course, would need to be defined in their lease agreements and would also require more work collecting those payments.

The reason is for that amount, that's all the attorneys would do on a contingency basis, and they only charged a fee if they collect on a lawsuit, The customer then asked if I would pay him a few dollars instead.

Goals - looking to expand/grow and move out to the next hack or hunker down and collect cash flow? 

First of all, as someone very very very remote from IT/tech world, it's going to be quite a challenge for me to get my site SEO optimized.

The second option is that she go to court, where she will lose, you get a judgment for everything owed including cleaning and repairs, and then you send her to collections where it will prevent her from qualifying for another rental, getting a car loan, etc.