I'm a 26 year old from Long Island hoping to acquire my first rental property by the end of the year.

.: Property managers, how do you collect rent from tenants, keep your management fee, and send the remainder to the owner without it reflecting as if you received the full rental income in your bank account?

You are losing money on both properties. 

They had about 90k into the property.

When I worked with a property management company, we had someone buy a unit (single family) that had a STR and marketed it as a STR.

I'm looking to exchange a multi-use property I own in the Bay Area for a multifamily property in Phoenix (looking at 15-19 units).

I would look at the DSCR loan as the first option.By the way, I suspect you are going to be disappointed by any refi appraisals   ADUs typically appraise poorly   JADUs can lower the property value Vs having the space as part of the primary unit.  

Driving by a property today to see if makes sense to walk.

With that bank taking on the loans of all of our rental properties we decided that we were comfortable switching to that bank. 

I have reached out and spoken with the HOA management property manager myself, and just keep getting BS excuses and no sense of urgency on this matter.