From my experience working with over 400 investors, I’d recommend starting with house hacking—ideally a fourplex if you find a good deal, but a duplex works too.

If you do, you should expect a very aggressive challenge by the IRS.At $350K of combined value it might be worth the cost to get a segregation study if you intend to keep these a long time.

Then sat still except for a subdivision development which has a long lead time.Just bringing on line as a 75 acre country subdivision.  

These properties are tenant-ready properties and support long-term growth. 

Another possibility I looked into is simply leave the current SFH as is since we have long term tenant, but build ADUs on the lot.

Some areas on Long Island tend to appreciate even more. 

The property then appraised for 190k which was good news since we didn't overspend. 

That is because they are looking at the long term view. 

Department of Housing and Urban Development (HUD) Secretary has brought renewed attention to a long-debated policy move: the potential privatization of Fannie Mae and Freddie Mac.

I would recommend you begin researching Chicago based meetups as there are a bunch of really good ones.