So, I reached out to a local brokerage, and they referred me to an agent with significant experience.This man has built a $30 million portfolio himself, and in just a couple of meetings, he completely shifted my perspective.

If you are calling the licensed guy off the one single van that drives by or was referred to you..

You definitely want to use a thorough screening method like rentprep.com that gets their income, credit, background check, and call at least 3 references (make sure to verify them by address/job and then their name).  

In general, I would say Kitchen, Bathrooms and any deferred maintenance should be your focused items. 

However, aside from that, I couldn’t find much information about them, and the only online presence seems to be the wife’s LinkedIn profile (though I’ve never met her in person and am just going off her profile picture on Zillow).After submitting the application through Zillow, we attached our income (two months of pay stubs for each of us from our current jobs), work references, credit and criminal background, rental history, and the contact info for our current landlord (who just so happens to be my fiancé’s father).

Hey Jessie --what other passive RE models are you referring to?

Quote from @Erick Pena: A "good" rental property is one that covers all expenses (mortgage, taxes, insurance, maintenance, property management fees, and any other costs) and still leave a surplus (commonly referred to as cash flow).Calculate cash flow as: Cash Flow = Rental Income − Operating Expenses − DebtThere's much more to it, but that's the basic idea.

Property management companies and contractors are the people in your business who make or break you.I will send you a private message to refer you to a property management company that is doing good for me.Don't let the bad experience sway you away from real estate.

If you need references for either of them in San Diego, let me know.

You reference taking out a HELOC and those are generally provided when the property is in your personal name, which I don't recommend for investment properties.Overall, it sounds as if you're tired of dealing with "long distance" ownership.