@Garrett Brown   I am going to focus in on this from your original post: I think identifying these markets that have a history of vacation rentals (so STR regulations are not worried about) If you believe a particular municipalities history of vacation rentals protects you against STR regulations you are mistaken.

You can suggest performing background checks, credit assessments, or offering a higher down payment to mitigate risk.### 6.

I would use cleaning services but it's my understanding I could use more than one company over the course of the year to limit how many hours one company spends on it.I'm looking into a utilitarian STR more for business travelers, so this won't be one where everything is perfect, it's bound to accumulate wear and tear I think.The STR would be out of state, but I plan to travel there for probably two weeks a year where I would perform many repairs myself.

If the tenant breaks their lease after three months, you are obligated to find a new renter, only charge the original tenant for rent up until the new tenant takes over, and then refund any unused funds.

3) Fair Market Rent: S8 was originally designed for affordable housing, so included ALL utilities.

You are INVESTING here, that means YOU are the one taking the risks of loss because YOU are the one with something to gain by the investment performing.

A two person partnership at 50-50% each has been often described as legal malpractice.Consider having persons assume the roles they will actually perform and document that role:The guy who finds the deal is the owner.

My original question was either to open llc in california and do  foregin entity in the state i'm buying property or the other way around.  

Also, may have instances in which if you go over a certain amount of useable sf you may have to fire suppress a building that would not originally have to be since it hit that minimum space requirement.

As a general legal theory, when the parties act in reliance on a written agreement and perform on its terms, the agreement is enforceable, even if it is very badly worded.