When all the dust settles, and the  person searching is tired and discouraged and gives up, Jerry may not have bought  a single lot, but he's made some money from the training he sold you, which was his main goal from the beginning!

The IRS changed how they treat single-member LLCs (solopreneurs like myself) and I expect there will be more changes like in Illinois coming. 

You cannot even apply for an STR permit on a single family home until after you've owned it for five years (and there is no guarantee you will get the permit).

We have multiple single family rentals in Cahokia Heights that we purchased about 1-1/2 years ago. 

I have recently bought a 2 bedroom single family in Cahokia.

Their first project...a neighborhood of single-family homes...yielded a steady 8% ROI in its first year.2.

That comment also seemed to imply that you don't report the rental on Schedule E if you have an LLC, but that's not correct, with a single member LLC it still goes on Schedule E."

I was insured through NREIG when it was a single rental to one family but now since I have transferred to room they dropped me.

Another lesson I’ve learned is that buying a single family home as my primary residence to later lease to a tenant is a bad strategy unless I’m purchasing the property at a really low price.

Purchase price: $186,000 Cash invested: $188,000 Bought a single family rental in West Buechel