I currently have my eyes on a fourplex for $500k, which according to my calculations will cashflow ~$350 with me living in one of the units, and then ~$1,850 should I decide to move out and rent my unit (this accounts for mortgage payments based on a 3.5% down FHA loan, insurance, property tax, repairs, capX, and vacancy).

Even without eyes on the unit...something's affecting the desirability or possibly the qualification criteria is difficult to meet?

But that's an emergency in my eyes).

I typically advised my clients to use 85% - 90% of Zillow's estimated rent.Craigslist is also good - Just make sure you are comparing apples to apples 🍎 As @Lee Ripma mentioned and that I confirmed with you, MF rent less than SFH.Continue to put in the work and your eyes will eventually be trained to spot great deals from 1 mile away 😀.Rentometer is pretty accurate and I rely solely on it for years before I became a Realtor.BP Insight is also not 100% accurate, especially for Multi-Family.Once you crush your numbers and you want to confirm your numbers on a property that checked your criteria, then reach out to your Realtor for comparable as this is part of their job and fiduciary duty to you as their client.You have the right mindset and attitude.Keep crushing the numbers man!

A year down the road, in the eyes of a lender you may be more attractive to get that DSCR because you have a history on paper of managing a rentals and could count use even other more convential loans (lower down payment) and count the properties potential income even tho it's not DSCR loan.

At the same time is good to keep an eye on the rental market.

I deal with this literally every day of the week... title companies just don't record documents without crossing their Tees and dotting their eyes.. and on top of it.. even if you have clear and concise language in the operating agreement that allows a specific person to sign for the company ( like I do in all my LLC operating agreements) they still want other members to sign or sign resolutions.. they don't bother to read the operating agreement they just default to having all members sign.. and for me with off shore members that is impossible 99% of the time.. its quite funny how we argue this like I said every single week..

I think the visual problem you may be having now, is with the high contrast of the smooth white window frames against the dark rough stone... it pulls your eye right to it, and there's nothing much else to grab your attention.My recommendation: First, redirect your attention to the entry/stoop.

Upgrade light fixtures, get a nice mirror and distract the eye with some bold staging items (towels, rug, maybe a faux plant). 

I have my eyes on a REO that needs a ton of TLC right now & I think I shall talk it over with my wife to see how she feels about it.