Now, I run a PM company.

This is what I am encountering, in the current Mortgage Industry.If you think you will go FHA, Conventional, FHA 203k, etc. and then Quit Claim the property, to a LLC, or a Land Trust you run the risk of the lender discovering a Title Transfer occurred and activating the "Acceleration Clause" or "Due on Sale Clause" that requires the loan to be paid in full, within 'x' number of days.

We run a Real Estate Notes Show where we speak with many of these types of investors teaching them different strategies. 

Any pricing-related tool offered by the OTA itself (think of VRBO, booking etc) is there to ensure you are getting heads in beds at any rate possible, just to ensure they are getting paid. 

Additionally if you're running an active business in the IRA the income will have to pay UBIT.   

Just off the top of my head, I wouldn't feel super comfortable with non-US properties because properties in the US are held to HUD code (at a minimum).

@Jay Hinrichs yes to my knowledge there are other states that changed regs.Off the top of my head.

Anyways, I think @Caleb Brown hit the nail on the head.

You will probably run into some issues and need to budget for that.You budgeted 5k for unforeseen expenses on a 4000sft home.

And with that again, nail hit squarely on the head.