You want both a title search and title insurance.

Trying to figure out what I need to do as LL - going to up my insurance,  what clauses should go in the lease?

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?

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

A private money or hard money lender is going to want to see that you're financially stable and have some 'skin in the game' so to speak, with some of your own capital. 

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.