I'm the VP of a roofing company in South Florida and work with a few good PM companies on a regular basis, a lot of bad ones too.There are good and bad PMs in each of those companies. 

Unfortunately I feel like a new roof is going to be pretty standard on the things I'm looking at so it might just have to get done on a regular basis.

Is your income considered variable in nature depending on job sites and that you do not work a set amount of hours per week?

In a stable free economy the natural tendency is for prices to go down not up.

And while yes, no one has the same pricing (combination of factors), I also continue to check on a regular basis our rankings and how we "present" on total costs per stay vs. our competitors.My gut says there is price creep and we might have a ways to go before the market really corrects.

What this stems from is that the IRS requires that a taxpayer trace interest expense to the nature of how the proceeds are used. 

Most likely the state where the property is located is where lawsuits would be brought if they are something for personal injury like a trip and fall or something of that nature because the “cause of action” arose in that state.

Please keep in mind investors, not every deal that you place under contract will close - that's just the nature of the beast when it comes to investing. 

Additionally, I understand the risks associated with obtaining hard cash and working with hard money lenders, including higher interest rates due to the short term nature of the loan as well as the risk involved.

But tell them what you are doing precisely - vacation rentals, not regular rentals.