Regarding BRRRing OOS - it can be very dangerous:(Too many newbies take contractors and agents at their word, when "trust, but verify" is extremely important.Given you're in Chicago, would recommend you plan 2 trips for a BRRRR:1) Initial walk-thru with contractor(s), which you should video for documentation & accountability.2) Final walk-thru BEFORE paying out final amounts to contractor(s). 

I pay for prop stream and love the amount of detail you can add into a search. 

And the amount of cash invested suggests you got a conventional, residential loan that allows you to house hack, is that accurate?

However, I have a good amount of friends who have made WA work very well for them.

I'd strongly recommend against a single family home and only target properties with at least 2 units otherwise it'll be difficult to cashflow in this high interest rate environment unless you plan on using a large amount of liquidity in the purchase.

Here in Colorado, you need to have a real estate license, and in order to get your license you need to go through what basically amounts to an apprenticeship for two years (associate), before you can have your own firm.  

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Separately, if you're eligible, you might be able to contribute $7,000 (for 2025 if under 50) to your own traditional IRA and deduct that amount from your income.

For this I’ve taken the payment amount of the second loan and included it as an additional monthly expense.

How long will it take you to accumulate the same amount of knowledge in Cleveland?