15% down with no STR experience - you're going to have to pay a price for that.

In my firm, you would probably pay around $3,500 for this tax preparation, including Form 3115.

Example, a short pay history - non-redeeming factor, a 25% down payment, a redeeming factor to counter the short pay history.

What if a tenant fails to pay rent, leaves $2,000 in cleaning and repairs, and it takes another month to rent?

, what legal documents should I pay attention to and why?

class action is what you see on TV  unless there is insurance money to go after you guys are going to have to pay a LARGE retainer to engage an attorney.. and if your deposits are only 40k or so Suing is a waste of time and money for any litigation that small

Fix the problem and make them pay for it.   

I would rather invest in safe markets that produce a good return, then I can use that income to pay for a vacation anywhere in the world.I'm very pessimistic about the STR market in Hawaii.

Keep in mind you will probably have a deductable to pay first.

This means that you will probably need to pay registration and filing fees in at least 2 states if you don’t buy CA property as a CA resident.Any lawsuits should be limited to the assets of the LLC and not your personal assets (assuming you run the LLC appropriately and the corporate veil is not pierced, some debate as to SMLLC).