My numbers are run with an FHA loan that considers factors Is the 50% rule too conservative, or are there simply not good buys right now in Chicago.

I'm finally at the point where I feel it's necessary to simply jump in the deep end and go for it.  

It is simply time and sifting through 5000 properties is something I may not have time to do well however the VA idea is an option! 

Or is this a waiver I can simply add in to the lease if they get injured using the weighs?  

You should simply be looking for what is a "good deal" now.

I recently discovered this site while trying to learn the ropes and i'm still feeling my way around.

Most of my investor clients like to see a potential profit of 18% or more (total cost to buy + cost to renovate + cost to sell = 82% of future sales price).For buy and hold properties, simply try to find something at the appropriate cap rate or better.

More simply put as a buy-n-hold this looks likes a good deal.

If that's your plan, I agree with @Jeremy Pace, that you should simply explain to agent what you want and exactly how much you want to spend to get it.I've learned that statements like "I want a good deal" or "I want something inexpensive that needs work" are too broad for an agent to get a good idea of what you want. 

I was leaning towards building simply because I wanted to 'max out' what the insurance company would give.