However, I could be wrong and would love to understand why.

Nothing wrong with that, but I so much prefer the the monthly cashflow + possibility of appreciation + tenants paying my mortgages.

It took the guess work out of the process and if anything goes wrong, she will be there to back me up.

It could be the wrong way of thinking, but I figured anything that had positive cashflow and gained me experience would be a win.As an outdoorsman, I love my job, and plan to stick with it for the foreseeable future, but I yearn to gain financial independence and indulge in my hobbies and be a family man when that time comes.

Take a few years off, chase your passions and your dreams, hustle, make money, prove haters wrong, and if all else fails, school will still be there.Hope this helps, and all the best.Happy Hustling.

@Lou LaMedica my mom is a wegman addict :) they actually live close to the town center where wegmans is located ( I want to say its woodbridge town center but could be wrong, they have a bunch of restaurants/bars there). 

What am I doing wrong?

The way most real estate deals work now is that highly leveraged purchases have little cash flow, unless there is something wrong, like located in war zone, deferred maintenance, environmental problems.

But that is wrong, and not a good way to build a sustained business or solid relationships.Both can be a great way to go in any market. 

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.