We currently own/manage properties across a few states including Hawaii so we aren't new to managing short term/mid term rentals.

Try interviewing at least three managers.1.

However, my true goal has always been to develop, buy, and manage real estate—something I’ve dreamed about since I was 12 years old.

Since you mentioned you're working 9-5, I’d suggest look into turnkey rental and considering property managers to help manage you’re property.

I used it to list my properties, screen tenants, manage payments, send notifications, manage maintenance.

If you don't have the relationships, hire someone who does.This is why Brian Burke can go “large corporate” while I have to stay “small private”; he has the ability to MANAGE PEOPLE that I do not.  

The managers are non-communicative.

However, like most property managers, once in awhile they do have investors interested in selling and at that point, they may reach out to their clients about that sale. 

. - Property Management: No STR can be successful without quality cleaners and management.

I've asked my clients a similar question and have developed tools for them to minimize this, but I find there are a few different types of clients.Manager managed - these folks have no issues as they simply upload their year end statement from their property manager, their 1098 mortgage statement and any other one-off expenses they may have paid for outside of the management company.