Quote from @Matt McNabb: I'm a solid $400k/yr job in NYC and have $250k to begin investing as my first step into building a portfolio, although I don't have time to be a landlord so I have to account for management fees.  

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.The City of Detroit has 183 Neighborhoods we’ve analyzed.DM us if you’d like to discuss this logical approach in greater detail!

Ensure you account for expenses like maintenance, vacancy, or capital expenditures.

Do you also create a virtual account for those? 

I looked into your account,  and it is just as I suspected.

Some questions to consider:1) How much negative cashflow can your other income stream(s) support?

If you can’t do a 1031 to a non-income tax state, figure out a year when you will have lower income and tax rates ar as low as possible.

I'd be heavily focused on mitigating that future tax liabilty rather than directly supplementing that income.

I have some of the required funds in a HYSA, but will most likely need to draw from another account and I'm curious which method is the most efficient in terms of taxes/capital gains, penalties, loan repayments, etc.Based on my previous transactions in the market, I estimate ~$45k cash to close: $20k for the down payment, $15k for closing costs and prepaids, and $10k of starting reserves.

First, banks do not prefer W2 income over 1099 income at all.