People move here for lifestyle ( at least they say) and with a state that is 93% Caucasian we do not have a lot of the social issue that other states have...

My question is after I scale up and make enough cash flow to sustain my life style I’d like to quit this job.

Sometimes there is only so much you can do to the property to add so as a secondary acquisition goal we'll acquire locations that are key long term locations in strong markets that will have a competitive advantage in different market cycles even if the advantage isnt "pronounced," right at this moment (beach,lifestyle, transportation, education, path of progress, city initiatives for development, and etc areas).The active business, in your case (real estate agent) or lending can fund the investing into the future while you work on freeing yourself.The highest expense most people have is their housing expense so it makes sense to house hack early on in the game for many who have W2 jobs or are sole practitioners/gig workers.

I would not do this if your income is going down or you feel a layoff coming between you or your wife.This decision is more about career and lifestyle, than it is about math.. 

@Kyle Hassig I would spend more time create a vision and designing a business that supports the lifestyle I want.

I'm sure this has long been discussed already but I cannot count how often I will cover very basic principles in this area and someone will still enact the exact opposite approach in their lifestyle.

I'd pick the one that meets your lifestyle best.

At least until / unless you find something that requires you to access that equity you have (I assume you have equity -- if even from your down payment)So I say hold, as long as the negative isn't too great and doesn't impact your lifestyle.  

Despite gaining financial freedom, self-managing landlords still lose some level of lifestyle freedom by having to deal with certain things in-person.

Someone in an A class rental CANNOT afford the same lifestyle when laid off unless they have substantial savings to draw from because unemployment doesn't pay enough.