@Jared G.I'd focus less on what you absolutely hate and focus more on acquiring the skill set to achieve the goals you set for yourself.There's very much this cheap pop psychological belief in our society that some people are introverts, and some are extroverts, and an introvert can never acquire, no matter how hard he works,  the social skills than an extrovert has.

What does renting back to the homeowner do to them psychologically - they now rent the house they could not pay for? 

Wife and I met with an agent last night and he threw out 2 interesting ways of dealing with financing when house hacking small multi family's:1) Do a 10 year mortgage at insanely low interest, have the monthly payment barely covered, while paying down the loan and building equity super fast.or2) Doing the more traditional 30 year at higher interest, cash flowing strongly, while maintaining the option to pay extra if that's what you want.Going into the meeting, I had kind of assumed we'd stick with the 30 based on what I've read so far but...wouldn't it be awesome to build equity like that, pay so little interest, have the option to pull significant cash out using HELOC or cash-refi, and the psychological advantage of owning something quickly?

I'm curious as to the psychology involved with external security measures. 

@Ed McIverI have extensive experience on the seller side of what you're experiencing, please PM me if you'd like to discuss in deeper detail some of the processes and psychology of the situation. 

With graduate school (Industrial/Organizational Psychology; don't worry, nobody knows what it means) and the first few years in the workforce behind me I am getting serious about expanding more rapidly over the next 5-10 years. 

I know this book isn't a Real Estate Book, but I think it helps greatly with the Psychological change that you need to have to leave the J.O.B. and go for it on your own."

Getting an offer in right before a price drop sometimes helps take some psychological pressure off the Seller: they're already emotionally prepped by their agent (if their agent is doing his/her job) that a price drop is coming in a couple of days. 

What I'm getting at is that while a previous eviction is a red flag, sometimes there are psychological undertones that drove the tenant to such a position that are no longer present.If you're looking to possibly rent to someone with such a past, there really is nothing wrong with that.

They just went even higher....I think a lot of it had a  psychological angle...people were feeling so trapped and panicked that they needed some release, and since everyone had tons of money sitting in their house...why not?