Think high property crime, high tax suburbs, undesirable to good tenants, etc.

Being on Long Island Homes are not selling for $20k or in any zip code under 200k unless very undesirable location with massive amounts of work.

I even picked up the talent of asking why my offer wasn't accepted and adjusted and re-presented my offer, yet for some reason, it seems like an FHA loan is very undesirable to sellers in this market. 

Now having said that, he has gotten lazy lately with just stuffing units to gather rent so there are definitely some undesirable tenants that we’ll need to get out as we can afford to do so.

If its sub $1000 your probably in D class undesirable areas. 

My landlord experience:  I had what I'll call an "undesirable family" move into my SFH for rent.

Let's say you can afford only a $400k condo, but the only areas where condos are for sale in that price range are in somewhat undesirable, and you are accustomed to living in a more upscale city.

Not that office space will necessarily sit vacant, but market rates might drop significantly making it an undesirable purchase. 

Also it may have other undesirable things like rates, drugs/crime.

From a cashflow standpoint, it's very difficult to make something happen unless you significantly leverage an under-used property (example: adding a unit in a building in a basement, renting parking/storage space, etc.)) and/or purchase a fairly undesirable property and invest quite a bit to bring it up to snuff.That being said, there's certainly something to be said for living cheaper and getting an opportunity to learn the trade.If you think about it from the standpoint of price per door, owning a small plex (2-3 units) can still be interesting.Example (desirable neighborhoods excluding DT, Verdun, Saint-Henri Plateau and Villeray)2 br condo = +/-350k Cost per door: 350kDuplex = +/- 550k Cost per door: 275kTriplex = +/- 650k Cost per door: 217kBecause the bank will take into account the lease when looking at your ability to pay, you can apply for a larger mortgage with a plex and the cost per door comparatively goes down.