By then I was so mentally beyond that concept that I told him I'd rather live out of a cardboard box than work for somebody again. 

The first thing you need to do is train your thinking from a save/spend mentality to an entrepreneur/REI mentality.  

Since May 2017, I’ve listened to about 3-4 podcasts/week and have read tons of books (far more reading than I ever actually did at college) pertaining to not only real estate investing, but also negotiating, overcoming mental obstacles, business strategies, etc.

Something I value significantly is my mental sanity. 

I think that's more of an investor mentality to look at what the previous person paid and try to see if you can get the margin down.

Also mentally if I can give them what they want and they think they have won then really I have won if it's just money etc.Just like athletes on any given day no matter how well trained anyone is someone can get lucky and take you out.

But so hard to call it, AND be able to predict investor's sentiment/mentality and where they are willing to take the market.

It's better for you mentally and emotionally as well to continue to work, take on challenges and stay busy at some level. 

But since you didn't, the only way to not be late is to pay it online TODAY...if you'll send me an email, I'll set it up"Me mentally - WTF, just pay the rent already - you're a professionalSome days I wonder how these people think thing the world really works.

How much does that student loan debt weigh on you mentally?