I know the property taxes are horrendous, so i'd try to mitigate that by getting into a CHAP district to freeze my tax assessment.

freezes.

just read the fine print on HELOC"s  they can get called and or frozen.. not that it would happen but it could happen if markets got tight.. millions of them were called from 08 to 2010... most folks posting now were not doing business.So when you get the loan docs read them carefully I will 99% say there is a clause that the bank can unilaterly freeze or call these due with no notice  I bailed out a lot of flippers in those years who were in the middle of big rehabs and their helocs got frozen and they did not have the money to finish.not being negative just giving you a heads up since you said your very conservative.

We are in the northern part of Illinois so freezing pipes are a concern.  

I feel like I'm on information overload and will freeze up if they actually decide to meet with me.

Can you plant anything when the ground is going to freeze soon?

@Jeff Greenberg, I am curious - does California freeze commercial property values at the last purchase price similar to residential or rules are different for commercial? 

From experience I'm not convinced on the air purge method.Instead I use a 3/4 HP submersible pump in a 5 gallon bucket & pump fluid (usually the pink 'food grade' RV anti-freeze) through the lines.

An acquaintance recently bought a condo in Berlin, Germany with a 1.3% mortgage interest rate (to my amazement), so that's also appealing, although the city just approved a 5-year rent freeze. 

In colder climates that was a common solution to freezing issues.