I am trying to gauge when it is required to hire another person.

How many doors does everyone get before hiring management?

If I've learned anything is to hire slow and fire fast.

That’s what you’re hiring the PM for!

Hire the right contractor.

Consider solving all your dilemmas by hiring a good PM.

People how hire me understand that. 

I hired a handyman/contractor to fix some drywall for me in a master bath that I am fixing up as a rental.

However, I would also hire someone (project manager, realtor, etc...) to just "pop in" several times throughout the project to see the progress of the work  - almost like a consultant to you so you have "boots on the ground".

That way I doesn't look like I was just asking with no intent of hiring them.