As we see the inside, we inspect as we go, take notes and lots of pics of flaws/issues.

Structural Flaws.

@Norman BermanYour question is flawed because it does not specify what "good" means to you.

We have a SFH that has been having a number of minor plumbing problems, and now we have uncovered that one of the major drain lines (cast iron) has deteriorated and will need to be repaired.

Then, if the inspection uncovers an unknown, you can back out or renegotiate.

The one flaw, which is not judgmental of your position either, but rather a fact that bears itself out over and over, as pointed out by Nicholas Nassim Taleb, having studied his materials very carefully, is that with the black swan manifesting itself, as a bad roll of the dice in Vegas, I could end up not only cash poor, but house poor too at the same time, and then really in a bad position. 

The bad news is that your idea has a few major flaws besides the fact that you absolutely must disclosure your intent to any landlord according to the 2020 IL TLRO Tenant Landlord Residential Lease Ordinance - the most obvious of which is that you are leaving yourself as an individual open to enormous personal liability.

This logic could very well be flawed, however. 3) I am hoping it would be easier to attract a working professionals who want to minimize commuting times by living in Portland proper4) I am planning to hold the property long term and will eventually convert to a full time rental.

He's uses a formula uncovered 5 years ago while he attended an investor conference focused on identify "positive cash flow" properties.   

The only hiccup I've uncovered so far is a reverse mortgage on the property, which is well below the accepted offer.