Ideally you want to improve to the minimum it takes to make a descent rental for the area.  

A house hack is like that beginner run (but BRRR'ing, wholesaling, and out-of-state investing are more like double black diamonds).The fact of the matter is: real estate is often a high-stakes endeavor, and the more advanced strategies (like BRRR'ing, wholesaling, flipping, out of state investing, etc.) can easily bankrupt a beginner when they're executed poorly.Plus, HH'ing is an ideal strategy while you're young...when you're in your 20s/early 30s, it's pretty common to live with housemates (or to live in a duplex next to your tenants), but this arrangement becomes much less feasible once you get further into your 30s/40s (especially if you start a family).Now, having said all that, house hacking is not necessarily easy (if it were, everyone would do it!)...

If the rehab is a reasonable amount, it may be ideal to find a Private Lender and pay them interest.  

House-hacking is an ideal way to get started on your investment journey as it can help cover most of your mortgage expenses while you keep saving up.

Not ideal of course, but anyone that tells you that they didn't make mistakes when they started out is full of poop!

And YES, ideally the first property would have been FHA, so I'm not sure if that will be an option for the second - but even if not, I'd think you can get in for less than 20% if you're purchasing it as your primary residence (2 to 4 units).

Additionally, we appeal our taxes on all properties each year no matter what.Chicago has what seems to be an endless supply of multifamily properties that need to be renovated, which is ideal for our business model. 

If they say a week or something, ask if you can store their things somewhere (ideally in a garage or basement if you have one). 

1- I would need the monthly rate to be $2100 ideally, but could get away with only having to put 10% down if the appraiser would do an adjustment and list each unit at $2000.

However, I barely notice is because it practically blends-in the with the rug. oGet new lighter colored bed covers, ideally white. oLiving room is too dark.