I have friends that routinely complain about it.

They’re becoming more strict with the primary residence requirements.

I don’t have a strict timeline and it’s west of Cleveland (Lorain county). 

Banks that strictly follow Fannie/Freddie won't allow you to close in an LLC, but if you do a debt service ratio loan (this is nonQM, meaning not conforming conventional) you can.

Are you investing strictly for tax purposes?

Had strict timeline for delivery, they failed that too.

However, strict compliance with IRS rules is essential to avoid penalties and preserve the tax advantages.Best of luck with your investment!

I’m continuing to put out plenty of offers on various properties and exploring different approaches to see what gains traction.For this one, I’m considering proposing a rent-to-own/deal finance contract with strict contingencies—something like requiring monthly photo proof of bank loan payment, with the understanding that failure to comply would result in a loss of equity of the seller.

Yes, Chicago has strict regulations for short-term rentals, including mandatory registration and zoning restrictions.

Strictly speaking from a financial point of view multi family's almost always make more sense unless your walking into some equity in a single family.