A building from the civil war be completely retrofitted with new stuff and a 1990s building could be having capex like the water heater, roof and hvac needing a change.  

As the others have stated, anything halfway decent under 400k is moving quickly and anything move-in ready is being held for a few days after listing so the price can be driven up in a bidding war.

He will also be interesting to see the tug-of-war between the supply and demand dynamics with less housing available versus demand compared with the negative interest rate cap rate Delta as described above and which one will win out.  

Where are the war zones? 

There are numerous inexpensive ways to do this - BP, podcasts, ebooks, and web research.

@Guy Gimenez I believe you can have your credit pulled for mortgage applications numerous times in a set period -- 15 days or 30 days, I believe -- and those only count as one pull, so there's no major hit on your credit score for asking a couple different lenders for help as long as it's in a compact period.

Fact is we have a massive net unit shortage, and until everyone decides to have only 1 child in their lifetime or the rapture, maybe thermo-nuclear war, the numbers keep growing this problem. 

My reason is simple: Chicago is a tough market and you can lose your shirt due to reasons unique to Chicago and Illinois.Sing and dance all you want, but investment opportunities MUST be viewed in the context of two things: First, does it “hit your numbers” – which includes such non-numeric things as risk tolerance and goals, and; Second – and this is where you fall down in my book – what are the alternative investments that also “hit your numbers” but with less risk?

@David Song I have friends in Oakland experiencing similar bidding wars.

You don't get into price wars...i.e. provide your highest and best offer.2.