Surely the mighty NY real estate industry has stakeholders with deep pockets and an army of attorneys to work on this thing, no?

It's the biggest feeder city there is besides NYC and also one of the most glamorized tourist spots in recent years. 

Like anything when you hire a professional and thats all they do, they will be able to provide more insite in to bookkeeping and your industry that the ROI is way more than what you are paying them.  

He wasn't micromanaging he was spot-checking.

Attend local REI networking groups and meetups and connect with people in the industry. 

I’ve been investing and wholesaling here for ~7 years, it’s a great spot in my opinion.

I want to begin investing with a house hack, but more generally use this position (with it specifically being in the RE industry) as a jumping-off point for a career in investing, eventually full-time. 

I have spent a great deal of time operating in the construction industry as a company owner, and I know the processes and challenges that come with the job.

@Nick Sansivero, Spot on by @Bill B.. 

He can get all three by working in the property management industry.