These will determine what fits.

If I hire someone to do work on my rental property in California, and that person (either licensed or unlicensed) does not have their own worker's compensation insurance on themselves, must I provide it if they are an Independent Contractor - and how exactly does one determine if such a person is an employee or independent contractor? 

However, I'm wondering if the annual tax amount should actually be based on the projected ARV since that is what the county/city will be assessing when determining future property taxes.I recently purchased a property (non-brrrr) where I used the previous year's tax amounts while analyzing, and then the the county reassessed the property taxes based on the new purchase price.

With all this in mind, I would have to second @Brendan Miller's recommendation of heavily considering selling as it doesn't sound like there's much cash flow to offer an attractive reason to hold.The only other piece of this puzzle is to determine what your goal is so that you can effectively leverage the gains.

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 turned to the internet to search for possible avenues of success.