I don't recommend this for individuals but in corporate structures with perpetual life or that beyond the term of the agreement can be done.

Perpetual self signing tenants (When one kid graduation or drops out, they usually bring you a friend they want to replace the departing student)Best of luck!

What's interesting is that the OP is stereotyped and the OP doesn't like it.

A lot of what creeps in as far as no-nos is perpetuated by lenders with overlays. 

There are a few reasons that standout to me for why this might be:1) It seems that the extra rent collected by having a 3rd (and especially 4th) bedroom doesn't always proportionally add to the rent price relative to maybe a stereotypical price hike in buying a 3/2 vs a 2/1 (i.e. maybe a 2/1 rents for $750 and a 3/1 gets $900.

That's what happens in markets with high demand and perpetually limited supply; it is the nature of the beast.

Frankly, when I get frustrated because I can't find a deal sometimes I start thinking about it too; it's just that I have seen it play out so many times.And also, Milwaukee is trending and does not fit the old "cash flow market" stereotype anymore: 

While I understand that many of these experts have perpetually pessimistic views on society and the economy, it is undeniable that the market has been booming at the highest rate since the years leading up to the previous financial crisis.I understand from ample research on BP that many investment strategies are relatively unaffected by market dips and fluctuations because they are not typically reliant upon appreciation.

I tend to have a perpetual case of "getting-ready-to-get-ready", but it occurred to me the other day that I might just have a great opportunity right under my nose.I currently rent a room in a house that i live in part-time.  

Yet another person giving “airbnb” a stereotype when there are those of us out there that follow the rules and play ball with actual “vacation rentals” or in Paula case “short term rentals” for legitimate purposes; not pukers.