Matthew,Welcome to the community, I think we might know each other from a previous life!

I have had previous tenants use it both ways, but now I am a bit worried about mentioning family with all the Fair Housing stuff I have been reading. 

After graduating from college I kept my frugal student lifestyle, investing everything in real estate.

I am about ten months into my first job since graduating college in May of 2017.

Near Bascom and City College most are section 8 and transits hang around..... 

Are the current occupants the previous owners or are they just renters? 

We got it financed as a single family property as the guest house was put down as storage on the appraisal. 

I get no financial benefits and our daughter has 1 semester left in college. 

Roof may need some work and there is a 2 car garage in terrible condition that might need to be torn down to make room for tenant parking spots.Property 2: On market 90 dayslist- 199,900 (considering offer of 178k)Taxes- 5400Rents-975PITI-1600Good neighborhood but further from colleges and down town area than property 1. outdated building, black mold in attic needs to be removed, basement is in rough shape and needs to be overhauled.

I have JV'd with this flipper on previous deals and we split the profits based on a percentage of how much each of us had in the deal.