I'm a strong investor and property management makes me sick to my stomach.

If your family dynamic can stomach it, I'd recommend house-hacking (ie rent out rooms and/or units of a duplex, triplex, or fourplex).

You state that there’s a $100 delta in rent and market and then talk about $400 end state but we don’t know where you’re starting.Get it as close to market as possible that you can stomach, your tenants can handle, and feel you can clearly communicate when confronted.

Every time I’ve ever tried it, I’ve literally felt sick to my stomach.

Yeah I need to make sure my eyes aren't bigger than my stomach.

Therefore, it would be very difficult to get that price for this condo making the investment a little hard to stomach. 

I had a deal similar to this and just couldn't stomach the timeline, the unknowns, and the need to be liquid for upcoming deals. 

If your cf is 150/mo or less, then you’ll have to determine what you can stomach.

And I have no interest in knowing about other peoples struggles outside of my W2 and charity.My wife and I enjoy renovating our apartments to be repositioned- it is fun, but my wife doesn't have the stomach for the managing.

If you are just starting out I believe there's nothing wrong with buying a property that may be closer to market value but needs very little work done to be "rental ready".As an out of state investor I dont have the stomach to take on big rehab properties, instead I've found good condition homes that have made solid returns on purchase price