It seems like every single person who knows the comparable home sales in the area and understands that their teir house needs repairing (and I bet they would underestimate these costs) would ask at least $125,000.Is finding properties as hard as it sounds?

My current top choice is a 5 Unit for $140k.  

@Chan K Look into Dwolla and PayNearMe , give all the tenants 2 choice: pay at 7-11 for a $4 charge OR pay online for free,

I bet if you listen to BP podcasts for 3 straight days you will learn more than the Than Merrill seminar and BP podcast is free.

I've dedicated many of his songs to my wife when we were younglings dating.Lol.Anyways, Let's make some assumptions here before we tackle this multiple choice question you have posed.

I would never want to bet on speculation in this or any market.

Your best bet would be to check the property tax or zoning maps.

If you're a new investor with limited funds, you're best bet is to find the lower price point counties in the DC area and focus there- Prince George's County, Waldorf, Anne Arundel, Montgomery (certain areas), Baltimore, etc (really most of Southern MD is pretty decent)Trying to go into the District itself as a new investor can certainly be done, but a) prices are going to be higher than surrounding areas so for the same amount of money to spend you're going to do less houses, and b) it's harder to comp properties- DC property values can often vary block by block, proximity to metro station matters, finishes matter, whether or not they've 'dug out' the basement to increase ceiling height matters, the exterior style of property- federal, victorian, etc matters.  

@Tara Piantanida-Kelly   no Warzones or Ghettos in Wyoming or Oregon  good choices for out of state investing. at least for piece of mind :)

West Oakland is a great bet.