It will be even harder as a young person with no life experience, and particularly no experience buying real estate. 

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

You all not be able to raise rents 50%, the renter in place will not be able to afford it.

However, they go to far in being different.Your house looks great!

Seeing it was only elec as well that is strange. $295 in the winter if the heat is running the blower motor(s) all day could be justified for a larger 6-unit building but I'd have to see the historical elec charges to know.

I'm a new house hacker here. What paperwork should I keep a paper trail of to make things like taxes and other situations better/easier for myself? Like should I have a folder on my laptop for the tenant and keep a co...

Had I scaled faster, I wouldn't be where I am today--I'd probably be working a job somewhere and have a lot of investors hating me.

I expect that I may have excessive damage on this home as well. 

They probably want to be certain YOU are legit.Most of the scams I've seen are by non-owners. 

While you might be able to find an insurer who will accept it initially, it's just a matter of time before they cancel the policy; your expense will also be higher.