Chicago is literally comprised of micro neighborhoods & communities, and the decision to invest in any given area must be determined on a house by house, block by block, basis.

The title company now needs to determine whether the judgment attaches to the property. 

Don't use Zillow to determine your ARV.

You decide to have a cost segregation study performed and based on the study, your assets are split up between the following categories: Tangible Personal Property, 5-Year Useful Life, 15-Year Useful Life and 39-Year Useful Life. 5% of your assets were reclassified to Tangible Personal Property (to be fully expensed in year one), 10% of your assets were reclassified to a 5-Year Useful Life, 15% of your assets were reclassified to a 15-Year Useful Life and 70% was determined to stay with a 39-Year Useful Life.

I have been learning and researching for a few months now and I have determined I would like to get into a house-hack before I finish school.

I do have clients with great success but you need to have the right manager to help identifying locations and determine if something would fit for Section 8. 

You also need to determine if you need any Contents coverage (for your property at the location not the tenants) or Detached Structures (garage, shed, etc..)Good luck with the purchase

What all do we need to look at to determine if a market is good for wholesaling?

So location will be a major factor in determining the potential strategy for the park. 

I some lenders will still look at your FICO score and investment experience to determine the interest rate.