I am wondering if anyone has a handle on what the price per square foot for repairs should be assumed for fixers in southside of Chicago.  

For example: if the gain you are deferring would be classified as a short-term capital gain on that year's tax return, then when the deferral period ends (when you sell your investment in the QOF) any gain that should be recognized would be classified as a short-term capital gain.This is not meant to be a comprehensive list of all the details, but just a small summary of some of the main points I identified during my first read through the proposed regulations.I hope this is helpful!

Just my 2 cents but I always go conservative in my estimates and run an analysis of what needs fixing and how long it will last - heating systems, hw heater, roof, appliances, carpet/flooring, plumbing fixtures etc

Then look at this one: https://www.mass.gov/info-details/massachusetts-la...Massachusetts is very strict when it comes to landlords. 

Ask your agent and your lender to run a closing cost estimate for the different scenarios before you offer.

I am getting more comfortable with speaking to these individuals over the phone the more I do it and even meeting up with people for coffee to talk in more detail. 

You don't want to niggle over every last detail with excessive back and forth negotiating.

Fixed up, the home is estimated to be worth $130-140k, but we aren't sure of the condition of the inside at this point. 

I had TD forward me the paperwork that was submitted to them and as it turns out, it was one page with the entire amount requested in cash hand written in (I had typed in everything on their provided form in exact detail). 

@Ian Boyle it's hard to know without more detailed numbers.