Frankly I'm a bit jealous.The best way to learn a language is to just dive right and get wet; I'm willing to bet learning facets of real estate is no different.

Networking with local wholesalers at your REIA might be your best bet.

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?

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 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.  

So evaluate the "total" cost of looking somewhere else versus your area.

West Oakland is a great bet.

I would not bet on that to happen though not impossible.All those potential scenarios are correct, appraisals or length of loan, equity are all factors.