The neighbors get foreclosed on more than typical neighborhoods and that keeps values lower for longer.2) HOA association decides to levy a $20K assessment on all owners in the neighborhood in order to upgrade everyone's windows, decks, roofs, and siding.3) HOA increases monthly dues by $250 per month in lieu of a large special assessment. 

It sounds like the lower response rate of postcards vs the yellow letters is a good thing?  

It's higher in rougher areas and lower in nicer areas.

We are new flippers/wholesalers in Chicago but have access to a couple networks with turnkey properties.

Our numbers dont work out until about $500K is it unheard of to go in at such a lower offer?

@Brian Halstead,Sorry to hear about your troubles with your insurance broker.I work for Fenix Risk Management, an independent insurance agency licensed to do business in Florida with access to multiple carriers in multiple markets.

I use http://www.resimpli.com/They seem to be priced significantly lower and have great customer service.  

Patrick Philip feels kind of slim, but I know flip profits are lower now in general because the market is so hot .

I would never want to treat an investor as less than absolute gold and risk losing access to capital.  

I don't know wether I should go further upstate or even in New Jersey or Connecticut which would be a long drive, or invest out of state so I can get better cash flow for a lower initial purchase price, then eventually I can work my way to invest here(if that would even be worth it).