The PMS around here are pretty terrible, I've worked with a lot of the larger ones in Cleveland and I think they just take on more properties than they can effectively handle and don't hire enough additional employees to make it work. 

Supplement this far simpler entity approach by ensuring you have appropriate types and levels of insurance, you operate your business in a manner in which your conduct is not considered an exclusion in your policy, you work with licensed and insured vendors, you execute contracts with indemnification clauses with these same vendors/ require additional insured status &  maintain appropriate licensing and permits.

In addition to being my mentor, Chris had been asked to take the class on a “funding tour”.

You want to make this clear that additional items need to be purchased by the guests so they are aware.

These are professionals with additional training and a stricter code of ethics.

Does anyone know a property manager that supports small self-storage rentals in addition to residential rentals?

Your best route might be to buy a 2 to 4 unit property that you can live in and rent out the additional apartments.

Man, just in 3 years if you have the tenant leave every time, even without the negative cashflow, that alone can cost you an additional 20 or 30k.

Best to call city hall for the town you are buying in to see what if any rent control rules are in place. see link below if you require additional information and call the Jersey City Landlord Tenant relations office. https://www.jerseycitynj.gov/cityhall/HousingAndDevelopment/...Jersey City CPI chart on recommended rent increases: https://cdnsm5-hosted.civiclive.com/UserFiles/Servers/Server...The state with the highest eviction rate in the country right now is South Carolina. 

An emergency fund needs to be liquid, and immediately available to you in addition to being low risk and protecting principle.