BUT even then, the contract is valid, it just violated Portland regulations and the owner would owe the tenant the local Relocation Fee (penalty, which is steep). 

Ethical ConsiderationsYour concern about ethics is valid and shows you’re approaching this with integrity.

Those concerns are totally valid.

Because we are dependant, for the most part, on word of mouth recommendations it is vital that our recommendations are valid. 

If the only MFH options you're finding are in areas you're not comfortable with, it might be worth focusing on a duplex in a better neighborhood.Saving up for a larger property later is a valid approach too, but keep in mind that real estate tends to appreciate over time, and waiting might make it harder to enter the market later.

All very valid points! 

Also, many PadSplit properties have bedrooms that are created via flex walls that wouldn't meet the definition of a bedroom in an appraisal, so many PadSplit owners may think their property is worth a certain a mount based on a bed count that's not valid. 

As time goes on, if you talk to enough people, you will understand who has valid perspectives.

If you move for a valid reason like new job, you can pro-rate your gains exclusion.

It sounds like you're at a crossroads between two strategies—both of which have valid points.