., without having to go to the state where it's located and asking around, i say this because there has to be a good way to estimate these things before going deep into the dealAny insights on this guys?

Are there any potential red flags I should be aware of?

I know, there are plenty of red flags there, but I do believe it is worth the risk when I consider how happy it makes my wife, how life-changing it will be for the family, how minor the financial impact will be on me, and how it gives me the opportunity to practice the steps of real estate investing with forgiving tenants.Finally, I am going to attempt to self manage as nothing comes close to cash-flowing if you include PM costs.

I wasn't sure if asking my FHA lender about switching it to commercial will raise red flags.

Gaps in rent payments or undisclosed tenant issues should have been red flags.It’s good to see the OP trying to help their client navigate this, as acting promptly is critical for any chance of recovery.

I will be managing the property and have done a deep dive in all things real estate - screening, leases, Oregon tenant laws, etc.

Don't see any major red flags here, so long as you are comfortable in the low income space.

The fact that you've "put over 5 offers on houses since February" and moved to a different strategy is a huge red flag for me.

Build an SMB on top of your real estate (the reverse of #2)Short-term rentals and high owner-participation real estate businesses can have great returns.Obviously not for you if you just want passive RE.We are in the deep end here, where each case should be judged on its own facts and merits by your CPA.You should hire a professional to review your particular situation before you make an investment.

One of the biggest red flags I have as a lender (who lends my own money as well as secondary market loan) is when a rookie tells me there goal is to buy 10, 20, whatever properties in the next year. my next question is how many do you own currently?