Some comments, take with a grain of salt!  

just my add to the story, when we bought a house(wa state) the brand new roof was a big deal for us and we were super happy to dont worry about it for at least 10-15 years and now we dont know what to do because even after spraying the mold you still gonna be able to see the stains on and it will come up on a inspection when we try to sell the house.

Please be careful with this one.Again, I might be reading between words, so you might want to read this with a pinch of salt. 

I’m thinking the best option for on market deals to house hack would be a home with a  mother-in-law and there are quite a few north of Salt Lake City where I’m looking.  

To our dismay, house has been vandalized with spray paint of gang signs on the interior walls and the back door kicked in.

That being said I'm a full fledge rookie with no experience so take what I say with a grain of salt.

Unless these people that are asking the what-ifs are successful real estate investors I would take their advice with a grain of salt.

Hi Everyone,In a few weeks I'll be heading back to Salt Lake City to start investing there.

Grass and weeds tend to grow in between pavers, you need to shovel and salt in the winter (especially in Chicago) and due to the freeze-thaw cycle the pavers tend to creep, move, bend and look unsightly after a short time (the frozen water expands, shifting the pavers around and out of alignment during the winter) All-in-all, I would imagine its a bit of a hassle, especially if people tend to enter through the garage. 

These were my first investments so take all of this with. grain of salt.