Jared,Take a look at these articles and I think you will be able to make a decision.http://www.themoneycommando.com/umbrella-policy-vs-llc-asset-protection-part-1/http://www.themoneycommando.com/umbrella-policy-vs-llc-asset-protection-part-2/ They dive into very detailed explanation as well as many risks/benefits & possible scenarios in which makes better financial sense.

I look at any investing as a financial diet, the same diet doesn't work for everybody. 

I just got a job as a financial analyst for the investment team at a commercial real estate management company.

Taking on underfunded investment properties can become very stressful financially and emotionally.Remember - if you decide to wade in now "Cash Flow is king" meaning it needs to cash flow when you buy it don't bet on being able to significantly increase the rent to improve cash flow.Good Luck!   

I'm looking for something that can handle the financials, track maintenance requests and payments, and deal with communication (announcements, message board, etc.)

Therefore, if you've invested - even at 15% discount - within the company, everything - financial, professional and income - takes a hit at the same time. 

If this was 2009-2011 I might say differently, but with this point in the market cycle coupled with your financial position, I'd say hold off.Banks won't let your parents cosign on an FHA multifamily, because it's an owner occupant only loan by the way.

Granted, tertiary markets have their own risks, but like all risks, understand and account for them in your financial planning and they can managed.I'm open to investments anywhere and am actively trying to build partnerships for larger deals where ever they are.  

I would like to start investing out of California in order to gain financial freedom.

I agree with @Chris Sellers that your next step is to begin narrowing down your market choices.My best advice:Be ruthless with the numbers - Be crystal clear on your financial objectives and how you'll measure success.