The bad: Needs updated baths, kitchens, refinished floors, paint, deck and landscaping at a minimum, basement is gross. 

I've got an approximately 500 sq foot deck that is in the location that would work well for addition, it is around 4 foot above grade, on a valley side of a roof.

Exceptions to that would be a game of multi-deck blackjack where the cards coming out of the deck influence what cards are still available (which is still irrelevant unless you've been keeping inventory and know which way the remaining deck is weighted).  

Some are even building HUD homes with 2x6 exterior walls, radiant barrier roof decking, a full house moisture barrier, low-e vinyl windows, extra roof/wall/floor insulation and high efficiency HVAC systems.

The son is a roofing contractor and this house needs a new roof and decking. 

I bought a 97 year old duplex with one permit on file, for a deck... 

After purchase, The roof leaks, I contacted the village to get the information of the contractor and  they informed me the roof did not pass inspection and the roof ridge lines are collapsing and certain areas of the roof need new decking and the shingles were not installed with underlayment.  

Old couches were tossed over the back deck railings, breaking them and then left lying in the back yard. 

They buy a decked out F350 they don't need and can't afford, live from job to job and the risk/reward of going to trial made it too risky to pursue.Live and learn.Oh and I suspect the problem is worse in rapidly growing areas.

I have been looking at 2-4 unit multifamily properties (3b/1.5b) in the Southington, CT area I did a site visit with my handyman.Property is in good shape new roof and deck, except for aluminum wiring and cosmetic items.This market has been very competitive the last year and decent properties don't stay on the market too long.