Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I'd run things by your local legal expert in landlord/tenant law. 

My primary concern with two separate leases is that it would be extremely challenging for you to remove a tenant via eviction for any reason because technically it is one unit.My recommendation is to provide one master leases signed by both groups of occupants.

if you're still evaluating software, I will be happy to connect with you with a solutions expert here at Buildium to go over what we offer. 

Verifying last 2 years of rental history and income extremely important to find the “best of the worst”.Make sure you understand the Class of properties you are looking at and the corresponding results to expect.PM us if you’d like to discuss this logical approach in greater detail!

Since the DSTs we consider seem to be conservatively underwritten, we believe the risk of losing our entire investment to be extremely low.

Not a Tax Expert.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

Why will likely determine how because if you are looking for cashflow vs. appreciation vs. quick capitalHow could it be househacking, brrrr, flip, long term -> You mentioned BRRRR, which is an awesome strategy but will only work in specific sectors of Chicagoland. finding the perfect brrrr in the current environment is extremely tough!

@Sandra Feurtado Matthew Irish-Jones is the most experienced and helpful Buffalo expert on here by far.