As Sean Wagner mentioned, the city of Chicago has adopted their own regulations on charging what's commonly referred to as a "security deposit" you need to do it another way. 

But after getting to a certain point in the process (keep in mind I haven't closed yet) I am left feeling extremely nervous with what the future holds on this property as far as some things go.

When converting common living areas into additional bedrooms, many DSCR lenders might view the property as non-conforming, which could pose challenges.

There is no given answer here, because the whole property needs to be relatively consistent.Kitchens and baths are the common answer, but if they are passable and you choose to invest in them anyways at the expense of peeling paint (or off putting exterior color) and overgrown landscaping, the appraiser and tenant will be walking up with a bad taste in their mouth, thereby not valuing the interior work you have done.But think about the general flow of someone looking to rent: more bedrooms will typically dictate more rent.  

Illegal basement units seem to be very common in this area.

these were common west coast rambler designs..

Follow up with sellers and buyers regularly to stay top-of-mind.By following these five rules, you can minimize most of the common challenges wholesalers face and set yourself up for success.

Here are the common exceptions:Relocation for Work: If your job requires you to move a significant distance from your current property (usually over 50 miles), you may qualify for a second FHA loan near your new workplace.Increase in Family Size: If your household has grown, and your current property no longer meets your family’s needs, you may qualify for a second FHA loan to purchase a larger home.Co-Borrower Separation: If you co-signed on an FHA loan and are no longer living in the property (e.g., after a divorce or separation), you may qualify for a second FHA loan for your primary residence.Non-Occupying Co-Borrower: If you were a co-signer but did not occupy the original property, you may qualify for another FHA loan as the primary borrower.Important Note: FHA guidelines typically require you to demonstrate that the current property will not meet your needs or is no longer feasible as your primary residence.2.

@Kieron Osullivan That was EXTREMELY helpful, thank you so much.

There is almost no understanding CPM- several multimillion dollar coliving start-ups have FAILED b/c they saw the demand for coliving w/out seeing the need for a respective form of property management (see HubHaus, Common, Starling, etc).