IE making sure the kitchen has can openers and a dish drying rack, picking up the mailbox key from the post office, assembling night stands, etc.Most of us manage remotely just fine, but most of us also visit our property once before going live to get it all setup. 

I have a 3 flat , and the stairs from the 2nd floor to the 3rd floor are wooden and sagging, maybe due to the building settling.

I just think it's harder for some people to save up plus I want to minimize surprises such as tenant racking up huge bills or suspect water usage (We are in closing now where seller just found out tenant hasn't been paying water bill and it's $1300 and tenant SD is only $800).

It has changed a lot since I first walked the wooden boardwalks. 

Either way, it would rent out well and I’d rack up those Marriott points.

Also winter weather is a great delay - ALL evictions are stayed Dec 18 - Jan 2, plus any day under 15 degrees, plus any day with inclement weather: https://www.cookcountysheriff.org/wp-content/uploads/2019/11/GO2019-01.pdf That alone racks up the sheriff backlog further.Sometimes if a tenant doesn't know anything, we can convince them to agree to move out in 30 days and the judge will then enter the order with a 30 day stay on that first court date.

The apartment is in good condition, with wooden floors and a standard kitchen.

My name is Travis and I am beginning this exhilarating and nerve racking  new life path. 

REI isn't easy it is hard work with some nerve racking decisions.  

Did not get to see the inside, but outside was grass overgrown, there was a wooden construction as part of the backyard fence (can be seen since it is an end of the street home), and looking inside the window looked empty inside.