Someone shut off the water main and left it sitting without making repairs.

@Jeffrey Gagnon  I hope that is not your main.

I have an applicant for my one-bedroom shared condo who lists his job as a property manager for a company that he owns.This property generally attracts college students and millennials just starting out.Why would a 50+ real estate professional want to rent from me?

my perusing of the municipal codes looks like you needed to pressure wash a tile roof and paint the exteriors as the main things. 

For me its gotta be higher COCROI and a better return off 20k especially if not in a attractable city.

You even attracted some that have a bug up their butt that private/hard money lenders actually exist.Not all lenders require skin in the game.

(House-hack)The main reason I'm getting into real estate is not only financial freedom for myself but to get my parents retired.

The main thing you need to do is make sure it cash flows without you living there.

As a state capitol, with OSU graduating 6000+ students a year and with the tax incentives offered that attract  and keep big business here, there is no shortage of need for multifamily housing.  

It's just too easy to get into the business, too much competition, not enough vetting from customers and , as a former contractor I can say this.....it CAN sometimes attract less than desirable characters.