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.

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

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

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

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

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.

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.

Losing $500/month before mentioning property management is a tough pill to swallow. 

You can also buy the Lease package from BiggerPockets located under MANAGE PROPERTIES.I recommend tailoring your lease, but I wouldn't get too excited about it until you have some experience. 

I did not include vacancy, repairs, management, and other cost, When determining what I was going to rent them out for.The one critical thing you never told us is what is the current rent and what is the current market rent.