I dont have a GOOD agent to rely on and compare comps . 

I wouldn't rely on much of a price drop with rate increase that's expected in Dec.

Philadelphia is made up of Neighborhoods and there numbers vary neighborhood to neighborhood.

The answer is going to vary by lender and according to your individual incomes as well as the structure of the buying organization. 

They are generally in Utah Idaho and Colorado so I am sure the reasons for the failure may vary.

I just got bit in the rear b/c Albany reassessed my property for what I paid for it (duh), which effectively doubled my property tax liability.I'm owner occupied, and with my first purchase I was primarily concerned with simply making sure the income covered operating expenses, and not terribly concerned w/ driving profit, but I was relying on the ~$200/mo I was making above cost to help subsidize fixing up the building, and now I'm about $50 south of the property costs.Paying $50 a month to live in my 4-unit isn't bad, but if this was a classic investment property, I'd be pretty ripped :)

Assuming you, the investor, must rely on outside money to make this happen, and you, the investor and owner/ occupier would be the property manager of the property, how would you approach sellers and/or private money investors to pitch this deal?

Speak to a few as the pricing and quality of service vary greatly in this industry.

The amount of taxes paid on a property will vary by location, and there can can also be some variance depending on whether the rental property is also being used as your primary residence.

In order to get out of your head, you've got to be able to rely on training, and that takes serious dedication and time.