@Evan Loader Not sure if you've tried these methods but i would try going to your local multifamily investor meets up, attending larger multifamily conferences and networking with Sponsors on social media platforms like BP and linkedlin. 

These types of tenants often do this because they don't want to save in advance, so they take the rent owed to you and use it to put down on their next home.Recommend you do a better job of communicating to the tenants that you will pursue every legal collection option if they don't pay last month's rent.Also, why are tenants NOT staying with you?

I have onsite management, but I manage reservations and communications remotely (and I have a full time job, so I really need the software to keep me organized, not the other way around, haha!).  

Most methods will do a bit of both - but will often highly favor one over the other.

Fix n flip is a quick turnaround interest only loan for a term of 6 to 24 months  The BRRR method is used for buy, rehab, rent and repeat with a more conventional mortgage structure.

You might Want to try opening verbal communication with the owner ahead of time.Perhaps having the owner come over and look at the things you took pictures of ahead of time, might/ might/ be an intelligent thing to do.

My property management has been good about day-to-day items like appliances and turn overs, but poor at comprehensive solve like exterior leaks and only one individual has been good at communicating with tenants.  

Communicate: Depending on your options, consider having a face-to-face conversation with your tenants.

Sounds like a lot of the issues are related to proper communication from BOTH sides,

Find Brandon's videos on YouTube for the "four square" method of analyzing homes and practice.