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.  

He then proceeds to inform us that the plumbing technician wont be able to get us a new tank and line installed until the 5th of October.

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.

Here's what I set aside per unit:Taxes:  ~ $100 per monthTurnover expense:  3.5% GSRWater/Sewer/Trash: $30-$45 per monthMaintenance: 12%Cap Ex: 2.5%Overhead: 1%Insurance: ~$25/mo.Debt service (100% leveraged): $350-$400EVERYTHING ABOVE is increased by 10% to account for vacancyAll told, each unit still cash flows between $100 and $200 per month.These are B-/C+ small MF properties.Note I do not pay for management as I self-manage, but that is offset by the increased debt service created by the 100% leverage.