I've heard there are area specific lending programs in Chicagoland.

@Malcolm ChelliahThe closest program that I am aware of for Jumbo is a max of $250k or 30% of the as completed renovation value, for the renovation costs.

My experience with real estate is part personal investing in publicly traded REITs, part classes from my Finance degree, and part derivatives based from my current job.

Here is a link to the proposed changes: Proposed Housing Ordinance ChangesThere are upcoming public meetings as well as a survey on their website where feedback can be given. for those that are interested.I am not sure how the city is trying to get the word out, but I am just hearing about this and I even previously had registered with them as a landlord.

Federal Fair Housing Act says: In buildings with four or more dwelling units and at least one elevator, all dwelling units and all public and common use areas are subject to the Act’s design and construction requirements.

I believe that I've heard that Chemical Bank and Hunington has some good programs as well.

There are insurance programs specifically for flipping that are month to month billing. 

They tend to be gentler, more responsible, and the programs naturally create a network to help keep your rooms filled.

Also, there are mentorship programs you can pay into as well. 

·Any entity chartered and lawfully doing business under the authority of any law of this state,another state, or the United States as a bank, savings bank, trust company, savings and loan association, or credit union, or a subsidiary of any such entity, which subsidiary is regulated by a federal banking agency and is owned and controlled by a depository institution·A consumer reporting agency that is in substantial compliance with the "Fair Credit Reporting Act"·Any political subdivision, or any governmental or other public entity, corporation, instrumentality, oragency, in or of the United States or any state·A college or university, or controlled entity of a college or university, as those terms are defined insection 1713.05 of the Revised Code·Any entity created solely for the purpose of securitizing loans secured by an interest in real estate, provide the entity does not service the loans·A Credit Union Service Organization holding a valid Letter of Exemption issued under O.R.C. 1322.05See O.R.C. 1322.04 for additional exemptions and exclusions and more details.