They also will likely not consider rental income that isn't being generated so you will probably have to have enough verifiable income to support the whole loan.

The 1% rule seems to apply still. 

(Without management fees it would look far better... but I’m out of state.)Is there a rule of thumb I can trot out to evaluate investments on a debt to monthly cash flow ratio.

Pleasant have different rules (no owner/occupants which violates their multi-family ordinance). 

What is a a good "rule of thumb" profit margin to shoot for when renting? 

I’m analyzing a property and it’s at a 1.6 rule or cash flowing at 170 if using the 50 % rule, but diving deeper it says it has a negative cash flow of 500 a month.

Looking for a great insurance broker who is experienced in handling house-hack situations.We may short-term-rent our primary-residence unit within SF regulations (up to 90 days a year), which we will also want to account for with insurance (been looking through posts here about some insurance companies cancelling people's homeowner's policies when they hear about STR setups so want to make sure we're above board and with a supportive insurance company).  

As for the sec deposit, follow MO rules, which allow for you to deduct unpaid rent from the deposit.

Constitution provides that "[t]he right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures, shall not be violated, and no Warrants shall issue, but upon probable cause, supported by Oath or affirmation, and particularly describing the place to be searched, and the persons or things to be seized."

Once the asset is paid off, the cash flow will actually support hiring a qualified professional who will make sure your LLC is managed the way it is supposed to be.