that makes sense, I want to get familiar with the tax strategy and hopefully venture into the STR world once I move in the next year or so, let's stay in touch!

Live in one of the units for 1 year and then move out.

I will also move my primary residence as the second single family rental property in the next six months.

You can then sell and take a proration of the gain (for the period of time you lived in it) tax free.Do a 1031 - Rent it for two years - move in and live in it for 3 years - You would get 60% of the gain tax free. 

In our experience, the S8 guru/scammers promote buying Class D properties and then renting them out to S8 voucher holders.It takes a lot of hustle and probably legally bribing the tenant with an appliance or two, to get them to move into a bad area.No telling how long they will stay either. 

I’m currently taking a “chance” on a basically turn key duplex which is something new for me.

-Using the city water bill, it's an issue at move-in and move-out to prorate usage since the tenancy won't line up with the billing periods.

Good afternoon all,I have a tenant who wants to move in her boyfriend who is currently on parole.

But curious, financially do you think this would be a mistake/bad move to take on a $750k home with the income that we earn?

I'm definitely new and I don't have all the logistics planned out this is just the vision now I'm trying to backwards engineer and figure out my steps I thought my first step would be to househack a 4-Plex on an FHA loan and then graduate to six or 12 units and then move on to bigger properties most likely outside of Chicago to your point. right now I am very confused this is the second time someone has said that four unit is not like a six or 12 but I'm not really sure in what ways is it the underwriting is it the management is it literally every aspect of it.