Any insights or wise souls out there with some advice...I'm all ears.  

And failure is failure, ignoble, miserable, and soul-crushing.

I will definitely do some soul searching and figure out whats most important to me.

It sounds like you need to do some serious soul searching. 

Not necessarily about RE; but an encouraging NY Times article today for great people on BP.FIRE movement — the acronym stands for financial independence, retire early — a way out of soul-sucking, time-stealing work and an economy fueled by consumerism.https://www.nytimes.com/2018/09/01/style/fire-financial-independence-retire-early.html?

@Braden Anderson I name them all for something unique about the house:The New House (it was a brand new build)The Soul House (it’s an old soul)The Jo House (interior looks like something Joanna Gains would decorate)The Pond House (backyard abuts a pond)Etc. haha it’s actually pretty fun

After I graduated, I got my real estate license and then got a soul sucking J-O-B as a leasing agent and quickly worked my way up to managing 100's of units and multiple buildings as a property manager.

Leaving the company in somebody else's hands when you end your shift.Say hello to managing minimum wage employees (may God have mercy on your soul!) 

If you have a bunch of rentals in a town where not a single soul is under the age of 70, I might be concerned about your ability to maintain rental success.

Hello out there to all of you brave souls!