And you get feedback at a level high enough to determine how to proceed. 

Highly suggest coming out to some of the local chicago IN-PERSON meetups! 

Spent a minute on their website and this in particular stood out to me as a red flag.

Here are some general guidelines: Lien Position1st Position LienEquityMinimum Down Payment of 20-25% (a 30% equity to sale price is preferred)Down Payment made in certified funds and not borrowedMaximum Funding of 70% ITV (Investment to Value)SeasoningMinimum of two monthly payments already made12 months or more preferredPayer CreditCredit Score of 650 or higherNo major derogatory trade lines (No 90-180+ days delinquent, foreclosure, repossession, bankruptcy, etc.)No decline in credit since purchase of businessTermsPrefer 60 months or lessMaximum of 72 monthsNo Balloon Payment preferredCash FlowBusiness has positive cash flow1.25 debt service coverage ratio preferred.DocumentationPersonal guarantee from a creditworthy individualStandard documents including Note, Security Agreement, and UCC-1 filing.Tax Returns on the business that substantiate profit and loss statements.OtherPayment history current and verifiablePayer Interview indicating buyer is satisfied with business and comfortable making paymentsMotivation for selling the note is not a result of a deteriorating businessConsideration of high risk businesses or geographic areasIn these situations, sometimes a partial is a better option. 

When we present a Subto for investors to buy, it has to have enough meat on the bone, all said and done, that the investor will still have equity and the property will cash flow.For instance, I have one I'm working right now, that has a high entry, because the seller wants some cash out to himself, but even with that, the buyer will wind up with $50,000 in equity.

Real estate has been a passion of mine for years, even while working in the high-tech industry.Together with my partners, we’re constantly on the lookout for our next exciting real estate adventure.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

The high end is the 20 or so co ops on 5th Avenue or Park Ave (one is on East End Avenue) that require liquid assets of $100 million + to gain board approval.  

This area was always a very high risk and should they rebuild?

Tossed around quite a bit and it isn't what it once was, but the value is still very high based on past performance and brand recognition.