@Nate Lawson  In Illinois on the seceretary of state website it takes about 10 minutes to make your LLC and it has perpetual exists immediately.

I always thought I would be max-leveraged and looking to grow perpetually.  

Stringent screening is great, but think you will likely need to relax your standards a bit to have the place not perpetually sitting empty.  

Great points above from  @Matthew Forbes, @Cary Plotkin and @Bruce G. as to not being able to raise rents perpetually with no value add.  

Please don't perpetuate negativity.  

Without stereotyping too much I'm guessing most section 8 tenants won't/can't pay a judgement if they stop paying rent.  

Discussions around house hacking and multi-family properties on the south side of the city were had since this property was opportunity for a FHA buyer.Normally people have a misunderstanding for the south side of Chicago, clouded by myths and stereotypes they forget that no matter where you go there is going to be negativity and bad pockets in neighborhoods.  

Depending on the answers above, your might want the easement to belong to the property and enure in perpetuity (if the neighbour is granting the easement to you or the driveway equally straddles both properties).  

I dont differentiate between the stereotypical flip vs BRRR type property because I want multiple exist strategies so I can mitigate my risks.

Like those stores in DC that are perpetually "GOING OUT OF BUSINESS!"