I have a W2 and can survive off it, so I never really needed my RE profits to spend on myself.

He scheduled maintenance and did quality control on cleans. 

Control the humidity, mold goes away. 

Flipping remotely is even a worse idea - you have no control over the scene and will likely be exploited because of it.  

At least we don’t have rent control and it’s in the IL constitution that rent control is illegal otherwise Chicago would for sure have it by now.

What are some considerations in finding a provider that offers checkbook control?

Many times they do not realize the adding of the adu makes their existing unit rent controlled.  

You will also quickly learn how to manage properties well instead of spending decades figuring it out like most investors.

I would spend more time improving and scaling your business so you can make more money quicker so that you can get the capital to invest in real estate.

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).