If you're already in the barn, you might as well milk the cow.

Camera (in phone)10, Grande Whole Milk Cappuccino.....

So are they proposing that the older, run down properties should be left to slumlords who want to just milk it for all it's worth? 

I have a lower paying job and make about 38000 a year driving milk truck and doing electric and plumbing repairs on buildings.

I would start looking at places just to get an idea of what's out there and milk the 1450$ / a month until I see a change starting to happen.

Can city water fill a milk jug every 10 seconds?

So a guy like Will picks up a multi, holds it for a long period, then when he has milked all there is...or when the land and sqft value strikes above a level that it makes financial sense, he redevelops into condos for an 8 figure payday.

Oh no, the former guys screwed up the renovation, it's going to cost a mint to do it right, you're going to have to bring in special people to fix all the screw-ups...milk it for all it's worth.

I recommend you check out mr. money mustache's site.  

The cash expenses are possibly true if the owner is milking the property for cash flow and skimping on capex/repairs (though the owner should accrue a reserve for those costs).