I am well aware of the class structure and pitfalls of renting to a weaker tenant base.

How common are these break in's in your area?   

I would just leave it, even though I'm sure it's somewhat of an eye soar because its not that common here in the city at least anymore. 

—JackHouse hacking is hands-down one of the most common and effective ways to get started when cash is tight — especially for someone in your position.Most people start by using an FHA loan (3.5% down) or conventional loan (as low as 5% down) to buy a duplex, triplex, or even a 4-unit.

Quote from @Eudith Vacio: haha that's a very common complaint against realtors!

If you choose to use this technique these are some of the Pitfalls to watch out for.

Any pitfalls to watch out for with tax basis, depreciation, or gift/estate complications down the road? 

Spending a few hundred dollars here can save months later.Most common paths:• Use & Occupancy “change of use”: If each unit already meets code (separate egress, fire separation, parking), the zoning office may grant a two-family designation through an administrative hearing.• Special hearing or special exception: Typical for R-zones; you’ll post the property, notify neighbors, and attend a public hearing.

Sales comparison A common method that compares the property to similar properties nearby and their relative prices.

If you acquire the properties as tenants in common(the title of the property will be in the name of you and your business partner) - There is no separate filing return required.