@Sam Leon When we acquire a MFH, it is typically as you describe - a hodgepodge of multiple generations of wiring from different providers strung along all nature of exterior and interior surfaces with random holes drilled in through the envelope.After we rewire one of our buildings, the resultant job quality greatly exceeds what any of the telecommunications providers subcontractors produce (most providers do not wire beyond the termination point these days).  

If such things surface in a claim, generally the company will simply retain the amount of premium that should have been paid from the proceeds.

Had obvious drainage issues, funky layout, etc.

Drainage transportation engineer for a consulting firm in Tempe AZ!

Now, all of this is just silly nonsense on the surface.

That is called market shift, not collapse, although I can understand ones confusion as on surface it may look very similar in the commercial space. 

Mind you, on the surface of it, those numbers don't sound too bad for buys-to-hold.

Find a state and area to specialize in - on the surface it seems New York seems extremely difficult to get started in?

Storm retention ponds and storm drainage system, any needed? 

A super bonus point, which would be expensive, and probably overkill, is to put in the drainage system you see near the footing of the foundation wall (labeled-4" perforated drainpipe).