Keep looking for duplexes, look in the surrounding areas, and add single family homes to your search that have some sort of separate living quarters. 

Option 1: 10% down, 4.375%, paying 2 points equaling $30K, P+I roughly $7525 + PMI of roughly 785 = $ 8310Option 2 20% down, 3.875%, paying a quarter point equaling $3700, P+I roughly $6301Option 1 would keep a significant amount more in our pockets (more than $125K) and get us very close to picking up another property and the difference in of 2K in cashflow would take nearly 7 years to balance outOption 2 would be over $300K out of pocket but would potentially give us the option of a very quick cash out refi as there is already a significant amount of equity as we went under contract last July and obvious market conditions.

I've recently met someone who was telling me about his fix and flip business and how he does one flip per quarter (4 per year) and based on the numbers that he's shared with me, he should gross around 50-60k per deal and tells me he's able to keep most of it because he's got a really good CPA.So, my question is, how do you screen and know when someone is able to provide you with that value-add service when you're not sure how or what that value-add service could be? 

Financing has nothing to do with taxation.

So with just that, and generally speaking, I would personally sell and put the money into a better investment for long term where you can mitigate some risks and make up your own rules, not be governed by an HOA or management company.Your other HUGE benefit to selling is the fact that you have lived there for the last 2 years which means you qualify for a capital gains tax exemption of $250k ($500k if filing jointly with wife) and would not have to go through the difficult process of a 1031 to avoid taxation on your gain.

Had a quarter-life crisis and decided to needed to get out of the Chicago winters. 

Keep an eye on investments and use leverage and make progress each quarter Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

In many cases, it is well meaning and experienced operators who begin by fudging numbers to "make the quarter" with the full intent of making up for the fudge in a subsequent quarter who in no time at all get neck deep in a Ponzi scheme.   

As of right now I am not ready to acquire my first property but I will be in an position to do so in the first quarter of 2023. 

However if using debt to buy the deal DSR is a little over a quarter short and obviously cash flow in negative, so not sure that would be an option unless bringing significantly more to the table.