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?

Thanks so much - I will post my progress. 

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.

@John Montgomery Congrats on getting close to negotiating your first deal...I would say the most important thing is to "know your objective"...There are a lot of great answers on this thread, but ultimately we are all making "shots in the dark" as to the best option for you because it's our perspective...This is still valuable, but can become very confusing because you don't know each person's perspective...MY Suggestion is to know your goal over the next 3-5 years...I will let you know a little about my perspective...I am a Rehabber and Have Been Buying and Rehabbing over the past 8 years here in Chicago...I've been in your shoes...I wanted to be the Big Shot and rehab deals straight out the gate(Little to No Money & No Experience but a few REI Boot Camps- basically No Experience)...To say I've had a lot of Failures during my 14 years of being involved in studying REI is an Understatement...If I was starting all over again, and my objective is to be able to build a robust REI Biz that can allow me to rehab 6-12 homes a year, wholesale 2-3 properties per month, and build a rental portfolio...I would first focus on getting good at one objective first...Generally most people start out wholesaling because it doesn't require the money or experience rehabbing or landlording requires...I would start with Wholesaling...go find 5-10 very good rehabbers and find out their Criteria for a Great Deal...Commit to building Value for them and ultimately a great relationship.With this you will already have buyers lined up, you know what areas to look for properties in, and you can research public record and see what they are paying for properties on the acquisition(and also ask them, but keep them honest by researching public record)...At this point become the best wholesaler to these rehabbers...you will learn a lot just in this process alone...How to evaluate Comps, Repair Values, Neighborhoods, etc...Which a great wholesaler will know how to do...It will make your deals easier to sell...Ultimately I would see which one of these Rehabber will be open to the idea of partnering/mentoring me on how to get into that arena...They may even allow you to follow the progress of their deals...Every deal has its surprises and over the course of 10-20 deals you will get a real life idea of what those surprises are, and even understand the "reason why" you calculate certain contingencies into deals and also what are the most costly mistakes or repairs to look for and avoid on deals...The value of this Experience will accelerate your learning curve...In my experience one mistake for a beginner can cost you a ton of money and even put you out of the rehab business.There is no way you can learn all the mistakes you must avoid by reading a book or taking a 3-day training program. 

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

I'm looking forward to learning from everyone and sharing my progress as I get started investing in Chicago.

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

Now get out there and don't post until you've interviewed some brokerages and tell us about your progress.

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.