Opportunity cost is a huge factor when considering this type of arrangement.Going with a 45 year old healthy person - what are premiums - how much do you stand to gain in short an long term given some hard number assumptions?

I'd suggest looking at Berwyn, specifically between 16th st and Roosevelt road, west of East Ave. 2-3 flats are reasonably priced and the walk to the blue line is only 4-5 blocks.  

from a contractor stand point if you are looking for piece work I would be charging 55$ per hour.

You have a leg to stand in because you have a greater chance of getting paid and armor to fight with because the tenant doesn't want to jeopardize their voucher.

We do direct mail; so everything from printing letters and envelopes, folding and stuffing those envelopes and dropping them off at the post office was all handled by us.

@Wayne Brooks I stand corrected.

As far as I know, Bruce put together an "All In or Fold" seminar in 2011, and told his investors to go all in while Bill McBride of Calculated Risk called the bottom of the housing market in Feb 2012.

To me, that would just mean that appraiser did a poor job and I won't stand for it.I am glad that you were able to get everyone to agree to a new appraisal.  

Put a mint or something bigger in the envelope so it stands out.

Further, in most jurisdictions nowadays, the court or trustee will check legal standing to bring about a foreclosure meaning they will check before moving to the next step in the process.