Essentially he wanted to live in his own place but didn't have the money and I figured buying a house with him at the time was a good investment.

Not impressed with other large institutional managers who are very light with boots on the ground and in many ways have the attidude they are assisting you in managing the property, not managing it for you.

I have 0 experience managing STR properties, but lots of experience using Airbnb from my travels 😅 I am halfway reading Avery Carl’s book on STR.

Do managers that advertise 8% only do 8% when there's a bundle of doors to manage?

Quote from @Don Bessette: I have a 30 plus year tenant that can not keep up with maintaining their unit, it is filthy inside and in desperate need of renovation, all systems are in good repair and I respond very quickly when issues are brought to my attention.It is also well below market rent, and they struggle to pay the current rate.Looking for suggestions on how to gently proceed with the notification to move. 

I am based in Virginia and licensing requirements here seem manageable.

My name is Adam King, and I am an avid real estate investor and life long San Diegan!

I graduated from college in May, and I am currently doing business development (sales) for a property management company while studying for my RE license.

I asked a ton of questions of both Fund and Grow and Plastiq, and I highly recommend you do the same because every deal and financial situation can look different. 

I also recommend you start looking for a professional property manager, at least until you educate yourself enough to run this solo.