Either it has been very poorly managed, the property is undesirable, or there is something else going on.  

However, from the resources I have read across the internet and here at biggerpockets, it seems that the politics (w/ condo boards, bank financing, reliance on other units) make it more of an undesirable property type for the rehabee.

The city can provide some nice opportunities but the good neighborhoods can be small and well defined.   2 blocks can mean the difference between a family area and a very undesirable area, that will have much lower rents and higher crime.  

Physical problems with the building or a bunch of undesirable tenants in the building.

Yes there are 3 ways you can do business there.Take the listing and market the heck out of it and spend thousands and hope you can work the seller down over time to close.Out of so many listings you take some will come in line and others will tell you to pound sand and take off the market.If you track your numbers and the large transaction closings still give you an excellent profit margin than it will work doing it this way.

It would be worth studying up on that technique.Because you know the area so well, presumably you have a solid understanding of which specific neighborhoods are most desirable (and un-desirable)--use that to zero in on properties in the most desirable areas.

I have lost FIVE pounds in a few weeks. 

Haul lumber, pound nails, sweep and do all the junk that hired labor does.

I would pound out your student loans as much as you can while you are still learning about REI.  

The new American posture that all consumers are victims and have no control over their personal choices has become a common theme since the start of the Obama era, and is still widely promoted by liberals as the reason that we need to move to more of a Bernie Sanders' socialist agenda.The real scandal that the PBS is afraid to talk aboutEqually damaging for the liberals who support and manage PBS is the 800 pound gorilla of real estate lies: that the American taxpayer is supporting the apartment industry.