Cash flow can be great if you manage it well and keep occupancy rates high, but factor in the added costs of management, cleaning, and potential vacancy dips.

It can provide a very misleading valuation.Your appreciation numbers reflect just below 4% a year (I used 8 year hold) on both properties which is below national average for this period and below what neighborhoodscout depicts for Chicago 10 year average. https://www.neighborhoodscout.com/il/chicago/real-estateLooking at this from the outside, I am missing a lot of details such as your interest rate, is there a prop tax benefit for long holds (by the way look up prop 13 for CA at some point as it may play a role in your decision to purchase once you relocate to San Diego), the neighborhood, appreciation potential going forward, any emotional attachment, etc.  

Turbotax isn't going to educate you so unless you'd like to educate yourself and potentially make some costly pitfalls, then I'd outsource.

What do contractors typically charge to come out to a potential property and walk through and fill out a SOW with pricing?    

Ensure you fully understand the fees, interest rates, and any potential prepayment penalties.4.

My advice would be to specifically retain a potential eviction attorney from the start, in order to be prepared for how this *may* go. 

Would going to local real estate meet ups be the best way to find potential investors I could partner with?

I'd focus on deciding what you want to do (flip-high risk, but potentially high return...or large loss; short term rental-more work, but higher return than long term rental; long term rental-less work than the other two, but lower return).Once you've decided which you want to do, then focus on getting the best house to meet your goal. 

The more that you talk the more potential buyers see what they are dealing with.Lori you purchased a property that was occupied.

You need to get in touch with a lawyer as soon as you can and figure out how to cut off the tenant/landlord relationship.