This past year they have started paying rent late to the point where the total accumulated time is about 3 months of back rent due.

Quote from @Tyler Garza: Deal :Duplex Home2 beds / unit2 baths / unit3,000 sqftAsking 300k60k downEst rent/yr - 31,2005% Vacancy20% Op ExpenseMortgage 240k assuming 7%Results: CF - 6,600Cocr - 11%Cap - 8%Looking at this for a buy and hold and trying to determine if I am analyzing this right For the best rates, to get near the 7% on a 2-4 family you are going to need to put down 25% instead of 20%. 

We have tons of new apartment complexes, so renting out apartments in quads is taking longer since they offer less amenities.

So demand for travel is lowering back to historic levels while the supply of STRs in many markets has increased by a lot.

Unless you monitor regulations full-time, staying compliant is nearly impossible—and a single mistake can cost more than years of property management fees.Properties don't pay rent—tenants do.

Renting out one side can help offset your mortgage, which is a huge advantage while you're building financial stability.

Includes a single family home (4 br) which was divided in two sections one of which is being rented.

The only one you really can't is raw land, because there are no costs to segregate.The bigger question is whether or not you can utilize the increased deductions from the cost segregation. 

You can add them but If you just go with what is active on furnished finder you will be right in the market range for the monthly rent and should cover the utilities + some.

You can find higher ROI (on paper) here and probably in other cities…but the probability of actually collecting rent significantly decreases.