-If you are set on selling off market and too investors, I recommend reaching out to all of the property managers in the area and see if they have clients.

However, I am unsure on how to go about finding the proper handyman/maintenance guy/management team to help run any out-of-state investments I make.

Network with property managers.

This will give you more opportunities and access to various opinions about the market and properties.As to cleaning services, you'd most likely hire a property manager who'll take care of that.

The ability to effectively self manage would depend on the scale you are trying to buy. 

3) Can I rent to my son and also treat him as the property manager? 

An experienced investment team can provide invaluable assistance in finding, vetting, inspecting, renovating, and managing properties effectively in your chosen market.

I’ve managed my fair share of properties, and the number one way I’ve gotten property management clients is by helping them solve a problem.

I currently have a rental property and am looking at getting my real estate license and building a property management and property maintenance company to serve my investments and potentially others.  

I do property management only that saves 10% and can be done while managing a W2 job.