Market is so constrained that it would have to be some horror movie type stuff to justify that kind of discount, and even then someone would still take it for 1/3 of that discount (at worst) nowadays

The equity capture at the buy is not talked about enough - a lot more people interested in cashflow and section 8, than buying a property at a 20%+ discount.

He told me I qualified for a discount based on expected income and that while the policy was about $350/month with my discount I only pay about $99/month.

If you are looking at a straight rental use a dscr loan.

There is latitude, but there are rules and guidelines.Can't be emphasized enough that it's best to get started with straight-shooting advisors & service-providers from the get-go.

I definitely planned on being upfront and maybe even offering discounts.  

I assume this because it is the only straight line value he retained in this event.My dad now has his son’s (Travis’s share) remaindership given back to him.  

That way you will be getting the information straight from the horses mouth.

In addition to calling owners and sending out letters as recommended above, I wouldn't discount developing broker relationships in the market you are looking to purchase a self storage facility. 

About / Members – Neighborhood Building Owner's Alliance (nboachicago.com)Another great spot to check out would be the Straight Up Chicago Investor's Podcast website which keeps an up-to-date list of meetups as well.