They have a different appetite for fix and flip risk since fix and flip lenders have data on who to lend to and investors filling to buy so they feel more comfortable in the fix and flip space. 

I'm aware of the fire suppression, ADA needs, etc. 

not sure if its helpful for your planning/designs......We generally need a mix of grade and dock doors, need 18'clears, must have fire suppression (doing flooring and carpet distribution usually) and generally need little to no office. 

(I'd likely need to displace the tenants in the existing 2 units)He said I could file an appeal with the state to just add the necessary fire suppression systems to the basement since the existing 2-family just had its smoke alarm system re-wired. 

is a much smaller market, so liquidity and lender appetite might be lower, but you could still carve out small multifamily deals if you have boots on the ground.For hard money lenders, you might check out Kiavi, Lima One, or local lenders like Civic or DLP Lending — but really, local investor meetups (look on BiggerPockets or local Facebook REI groups) can plug you into smaller private lenders too.

There are thousands of illegal and non-conforming units here in Chicago, but each investor needs to weigh their risk vs. reward appetite.  

Looking at historical absorption rates as a signal for seller vs buyer's market... it does feel like buyer appetite has slowed a bit in recent years, but could also look at it as more of a return to the normal pre-2020 levels if we zoom out!

In general, home sellers had less of an appetite for creative deals when they see such high dollar amounts on Zillow.

Price range is going to depend on what you can afford, your appetite for doing repairs, and the rent rates you can expect in your market.Jayme

Macroeconomics are suppressing spending, combined with a massive overbuilt supply of properties.