Based on what you all have said, over the next 5-10 years my primary pursuits will be to first and foremost maximize my education and income in my profession and secondarily to invest in my business from a cashflow perspective (buying practices and dental real estate, hiring new associates to run those practices, etc).

So I hired one of my cleaning ladies to make etched wine glasses for them. 

and think you hired them to be a consultant instead of a worker bee?

Some people WANT to do DMM, so they will find reasons why DMM is better, even when it isn't.Here is why I always suggest people to NEVER hire a marketing company.A bad marketing company .. wel.. they have no clients right?

To hire a VA, use upwork.comThere are software services that you can use to help automate the mailing process for this.

If he sees issues, you can always hire more inspectors/contractors to investigate further.  

If you are a start up doing this all yourself....or looking to hire your first team member....you have to gauge on when you are starting to feel overwhelmed and IF you can afford it. 

What’s the positives and negatives of hiring a CPA and is it really a must to have ?

Employees end up being hired not because they bring great value to the company and clients, but because they fill a role that needs filling yesterday. 

The best thing to do is hire a private detective.