I'm currently a senior in college and plan on graduating in the Spring with a degree in finance, and am currently still living with my parents and have no major expenses outside of paying for my car insurance and phone bill (Lucky, I know).Given all the experience and knowledge on this site, I was just curious what would be the best way for me to start out?

So we've been trying to find a better, more personal solution.We found a gentleman in Chicago whose run an insurance brokerage since 1991, and he seems to be one of the only local insurance brokers willing to help protect and insure properties that do Airbnb/vacation rentals.

Have you come across other quality STR insurance options?

NONOPayment Calculation Years 1-30 Principal & InterestMortgage InsuranceEstimated EscrowAmount can increase over timeEstimated Total Monthly PaymentEstimated Taxes, Insurance & AssessmentsAmount can increase over time See page 4 for detailsCosts at Closing Closing CostsCash to CloseCLOSING DISCLOSURE$836.31++--$836.31This estimate includes In escrow?

Weather it be the standard 1%, 70% rules or something unique that you have come up with.

I am currently working as a Licensed Insurance Agent in SoCal.  

3) Is there a usual or standard amount/percentage for the Option Fee, rent credits, and any other fees/charges?

My plan is to hold it as a rental, but the flood insurance premium might be a CF killer. 

Assuming that you're accounting for ALL expenses including vacancy, maintenance, CapEx, insurance, etc., then that is still a low return from the cash flow side of things. 

The GC was licensed and insured.