Plus, the easiest way out in life is to give up, documenting the journey will add one more level of accountability. 

@Ralphie HernandezDaniel Dietz nails it as far as my thinking, but I’ll add one more thing.

Once you add on the P&I, you're probably in the hole.Brian, insurance and taxes are not your only expenses, as I think you're aware.

Managing and holding properties with different LLCs will probably not add one bit of additional asset protection but will add administrative cost. having one management company to manage a large portfolio may make marketing sense but you have to be pretty large to leverage that.

It may sound nice to pay a 5% management fee but the extra fees can add up to be more than the other company that charges 10% with no add-on fees.

Assuming your state allows you to charge late fees, charge the late fees exactly as described in your lease every time rent is late--no exceptions.  ...if your lease doesn't already have a section like that, have an attorney help you add one...As others have mentioned, the late rent alone is reason enough to want to part ways with these tenants. 

Just add one other item to your DD: a Flood Zone review.Yes, it is generally more expensive to develop/build on a Flood Zone property. 

My 10-year goal is to own and operate 2-4 short-term rentals in lake-based vacation destinations and provide add-on hospitality services to further my mission and cash flow.

It is my understanding that the Zillow API is meant to be used as an add on to your own web site where you pull in and display additional property information from Zillow.

We do a Christmas letter at the end of the year thanking them for their support and add ons to our properties.