.- Insurance: Short-term rental insurance (beyond renters') can protect you from guest-related risks.- Licensing or Permits: Check if your area requires permits, as some cities have fees for short-term rental operators.Breakeven Analysis: To calculate your breakeven occupancy rate, add all monthly expenses (rent, utilities, cleaning, insurance, etc.).

Investing first and buying later provides financial freedom but may be time-consuming and costly.Good Luck!

All the usual creditor protections are thrown out the window depending on which BK court has jurisdiction.  

We see so many different entity structures for rental portfolios in our REI Bookkeeping Firm.Ensure it's simple enough for you to easily abide by the structure in your day-to-day operations (which your question is getting at).We've had bookkeeping clients with complicated structures that apparently protected them to the maximum degree but they didn't abide by the structure when conducting transactions in their business daily (lots of unintentional commingling).

Just make sure the builder’s risk policy is in place while the property is vacant and under construction to protect your investment.

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

Instead of increasing rent, I would look at having the security deposit increased to protect against wear and tear.

Make it clear that you’re prepared to go to court, potentially jeopardize his license, or report him to consumer protection services—or at least make it clear you’re considering these steps.

Also, @Joshua Stanton, how do you protect yourself/assets if you can not deed the property into an LLC? 

To protect yourselves, ask the sellers for written documentation confirming that the tenant is back-paying.