It's a lot of work upfront but once the team and systems are established it gets easier and as you get better you can expand to another city. 

Hiring a contractor to assist with repairs and a property management company to manage rental.

One of my friend happens to be a RE agent, landlord and a property manager himself and he seems to feel that as long as she pays rent on time and does not create nuisance, not to worry much and just keep do a quarterly property inspection.

We have two rentals rent by room and a househack duplex.

Will finish both tomorrow then work a shed site down below and a road around the property.  

It is an area you are likely more familiar with and closer to which could be helpful for your first investment and as @Sarah Kensinger metioned, you may be able to do a MTR.  

I have a pretty straight forward return with a W-2 and a K-1 from an LLC. 

I just know I don’t have the knowledge yet to find a deal and a lower price point is appealing for sure.

These are professionals with additional training and a stricter code of ethics.

So you give us contradiction and a deafening silence as to those who are too poor (no, insufficient, insurance) or are unwilling to pay/co-operate.Woolly thinking on your part, Jim.