Plus these insurance rate averaged $6,000 /year, so $500 / month...

The initial plan was to slowly rent out the spare rooms and renovate until a refinance/moving out and onto the next property made financial sense. 

The irony in most cases is those who spend excessively for complexed entity structures can't even articulate what they are protecting against and operate the underlying businesses recklessly (improper insurance, inadequate or no contracts etc.) and end up in trouble anyway.

The title insurance seems reasonable to me but its impossible to know for sure without having the property address. 

Their model seems to be to short term rent (3 months) to insurance companies and then pay 1 or 2 months rent (late) to the owner and eventually just quit paying. 

Your local S8 Housing Commission should have an info sheet on their website that shows their deductions if landlord chooses not to include electric, gas & water.Even more critical, your $680 mortgage amount, that you appear to be comparing to the S8 rent, should include ALL the other housing ownership costs: property taxes, insurance, vacancy/tenant nonperformance (S8 tenant may have to pay part of rent), maintenance & miscellaneous.Suggest you use the BP Calculator for this.

We're in the early stages of planning a garage conversion in Los Angeles.

In fact, JWB directly handled everything with the insurance and I got quickly the money.

So let’s say I have a Holding LLC in WY and an Operating LLC in MD where I plan to invest.

My question is for anyone that has house hack or is planning to, what’s your story?