A no show is an auto rejection.

That may be high, but one thing many of my clients are 'shocked' by is the overall cost for these type of projects even after giving them a summary of what to expect.If this was City of SD and you were bringing this to me based on what you have mentioned I would advise that you are unlikely to get this approved due in large part to the type and number of non-conforming features...the lot size is generally a 'no-go' without some specific reasons why it should be approved.

And a no-brainer to acquire an awesome Chicago property.Another option, instead of the HELOC might be to do a 203k refinance loan...then you wouldn't have to come out of pocket any money. 

This seems like a no brainer for 6k down but I just need some opinions.

If an investment house is a no go at $400,000 its probably still a no go at 2% less.

This might not generate enough bookings to carry my business, but in terms of marketing ROI I think this will end up being a no-brainer. 

High-interest loans, like most credit cards and personal loans, became a no-go as they don't provide value in the long run.

Is the fact that the property can pay for itself and still provide a little cashflow the first year with a steady rise after that a no brainer or what are we missing?

Combine that with almost zero used inventory it was a first time ever decision that was really a no-brainer. 

-------In 2013, my wife and I purchased a 1974 2-story "fixer" in Clovis, NM via a no-money down VA loan, which we poured our blood, sweat, and tears into for 3 years: refinishing the exterior, installing hardwood floors, upgrading countertops, repainting all the walls and trim, retiling showers, blowing out walls, replacing light fixtures, etc..