I am not comfortable offering a price based off of what potential rent is, knowing what rent is current.The big problem I have is that the three lowest rents are social security assisted living that have been there for 5+ years.

From there, I would filter down to the most motivated people who would take a very low price, perform a title search to check for liens and title issues, get a contractor to give a more accurate estimate for repairs and use that to refine my calculations, get the contract and necessary forms signed to secure the property and then finally market it to my buyers. 

I am currently looking to secure my first home for a fix and flip.

As part of the application, she provided documentation of the monthly social security awards for each of the three prospective tenants.  

Determine the billable items for the final accounting on the return (or retention of their security deposit.)

Don't waste so much time upfront until you have secured the option to purchase the property.

I have a good idea of how I want to get there, I’m just curious of other people’s paths to get there.My original goal with real estate was to provide additional income for retirement; have a couple paid off houses and help supplement retirement income from my 401k, social security (if it still exists), etc.

The lender is secured and will be paid at sale closing by the title company from your sale funds.

It seems to me that you would rather a secure financial position than to leverage your assets to make to increase your cashflow.

From there if there are any deductions that stem from the walk through provide an itemized list of any charges they will incur from their security deposit complete with pictures of any infractions.