(Foundation, etc)4) Black mold, asbestos, lead paint, other other costly repairs. 5) It need significant cosmetic repairs where the purchase price just isn't worth it. 6) They may have an odd layout of the rooms. 7) Non-compliant septic.8) Trouble with permits or tenants9) Listing agent has a poor or incorrect listing.

Both bathrooms need a complete remodel as well as the kitchen, the ceiling in 2 of the bed rooms are bowed (previous roof leak that was fixed) so new ceiling drywall, appliances, flooring, and paint throughout.

Expect to remodel kitchen and baths and put new floors down, paint, knock down a wall to open the floor plan. 

Power washing the exterior, repairing the driveway, and painting the front door What was the outcome?

Change out the used sheets with fresh ones, then take the used ones off-site.

Your pictures do not paint a picture of what I'm looking at.There is a renovated 2bed/1bath right around the corner for $1,050 and it has a decent floorplan.

Mortar, paint & bonding materials deteriorate leaving cracks, gaps, etc. which can be concerning to look at, but this is very often addressed with repointing.

To clarify another point @Tiarnan Gormley: I EMPHATICALLY disagree with any & all advice being given of: sit-tight..... wait..... be patient.... watch paint dry..... do nothing..... 

The tenant fails to pay their last month's rent and leaves the place needing new flooring and paint.

Adding paint and replacing flooring is not going to add much value in the typical case.