As I look to understand the economics of a deal I'm pursuing, I wanted to get recommendations for good multifamily insurance agents in North Florida.  

Your 401k would have to pay those assessments just like it would pay other expenses such as property taxes, property insurance, etc.

Make sure your insurance coverage covers your total value replacement and not the loan balance. 

Are the properties insured properly?

Another idea you may want to look into is whole life insurance.

You will need a copy of their license (if required in your state), as well as a copy their Liability insurance. 

My girlfriend and I have stable jobs with the government and we max out our retirement accounts (TSP, Roth IRA, HSA), and we’re now looking for ways to deploy our extra, after-tax savings.

Maybe I'm wrong, but considering I wouldn't be paying 2 mortgages, water bills, insurance ect. wouldn't it be safe to assume I could purchase a property with a slimmer profit margin?

The property is a 5 unit building with the following information: Rental income is $4,000 per month or $48,000 per year totalTaxes are $375 per month or $4,500 per year (this is higher than current but factoring in that they will increase)Estimated insurance is $200 per month or $2,400 per yearExpenses: Vacancy 8%Management 10%Other expenses Landlord pays water at $400 per month or $4,800 per year Realize this could be a cost savings in the future, but want to analyze as isGeneral maintenance (including minor repairs on property) including grass and pest control estimate at $300 per month or $3,600 per yearCapital reserves for Cap ex (appliances, windows (52 windows on building), roof, siding, etc. which I based on building a capitalization table based on useful life of items and number of units) at $460 per month or $5,520 per yearLoan: All in after down payment the loan would be for $300,000Assuming 7% interest rateAmortized over 20 yearsThus comes out to $2,325 per month or $27,900 per yearSummary Income Per Year:$48,000Property Exp.

You could potentially still live for free (your roommates pay your mortgage, taxes, insurance, expenses, etc.) and you are building equity at the same time by paying down your mortgage and you don't have to live with your parents.