IMO, such an approach will help overcome this initial disadvantage, but don't give up, you'll learn that real knowledge will overcome youth and often the lack of money.

From my experience so far and talking to other investors, there are a ton of cash buyers in the chicago market, especially the southside in the particular areas I'm looking to get in.My question to anyone who has experienced being a newbie in a hot market would be how did you overcome it, and find your first deal without compromising your criteria?

If that is too much of a commitment or a task with barriers that can not be overcome, perhaps this is not the asset class to work in.

Good Luck in overcoming the obstacles in your way!

The new opportunity needs to be good enough to overcome the dual transaction costs/work.I think a question we must continually ask ourselves about any of our properties is: Is this property the highest and best place for my money?

The problem is if you do not do your homework, you can get stuck in a cheaper property that is in the wrong area and the losses, vacancy and vandalism will be a perpetual loss that will be insurmountable to overcome.  

Now we did our homework to dig up this info and personally spoke to the new HOA management company and based on the information felt that it may be a rough year or two but afterwards - blue skies and strong equity in a very desirable area.We made an offer well under asking price based on the situation as we feel if overcome the purchase price in the area and growth potential is there. 

I had to work it into my schedule and make it a point to overcome as well.

But you have the "chicken and egg" problem to overcome first: how do you prove you're a "closer" when you can't get the time of day?

It makes a buyer's job harder to have to overcome these unrealistic appraisals.