Even though we hired a project manager, I want to be more involved in my deals.

All our prices were UNDER what the insurance company paid, and they still weren't low enough.So, owner went and hired someone to do the work cheaper than us. 3 months later they called us to take over and the job was a mess.

I probably didn’t elaborate well enough in my post.My income question was more meaning how do I know if it’s smart to invest in property with freelance income in a potentially volatile industry.

If they demand better performance, let them hire an A/C technician on their own dime and get a professional opinion, or they can terminate their lease early and move somewhere else.

I hired a licensed contractor to do the work but still ran into so many issues with the inspectors. 

Target areas with companies aggressively hiring college graduates, your rental pool will improve.

You can usually live in a favorable location for your lifestyle and either commute to a property or hire folks to do all of the heavy lifting for you.

A PM should be hired to alleviate the stress and responsibilities that come with being a landlord not with the idea solely on profit. 

If you want to be successful at short term rentals, learn guest relations or hire a property manager.

As for the manager I hope to hire, we plan to build him a house attached to the on-site office that will accommodate him, his wife, and his mother in law who are to serve as relief for him as needed.