Plan is so that he can retire and him and my Mom can be financially secure on rental income while my sister and I manage the properties in the trust. 

Most S8 tenants have a history of bad decisions and from all that, many have only learned how to game the system.We embrace S8 applicants, but screen them just like any other applicant.Many have an entitlement mentality and try to leverage their S8 voucher and pretend to be helpless:1) A percentage won't apply because they expect a landlord to waive application fees for them.2) Many cry broke and expect a landlord NOT to charge them a security deposit.3) Many of those same S8 tenants trying to avoid paying a security deposit, won't make an effort to call the list of nonprofits we send them that will pay their security deposit if they apply.4) A lot of them try to avoid paying for utilities.

Second example: I purchased a first lien note secured by a very run down shopping center in which the principal balance was $470,000 - I paid $255,000 for the note.  

Imagine closing on a vacation rental that can't secure a permit?

You will receive the security deposit in Checking but then transfer it to Savings.Savings: Hold the deposit here so it's separate from operating funds.

You are going to blow a lot of money for a false sense of security that a good insurance policy can protect you from and save you thousandsThe LLc is the most overused and money waster used on single family rentals.

Most investors  who pursue alternative lenders aren't able secure bank financing because they  lack the creditworthiness, experience or the deal doesn't pencil.

It could be helpful to have a real estate attorney look over these agreements for added security. 

I called VRBO customer service and was told, "Well, you have a security deposit. 

Why don't the banks simply charge a higher interest rate to secure the business and cover themselves?