At first I thought no, because he brings the contracting to the table and has relationships with subs but, I've done the self prepared DM marketing campaigns, taking phone calls, building rapport with prospects to sellers, finding the deal, building our team (lenders, title, insurance) for the past 6 months, and did not get paid for any of that work.

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. 

Let them proceed as they may. 

We plan to sell our current home and use the proceeds to pay off the credit cards dragging our credit down and the lender we work with has verified doing so will raise our credit to where it needs to be. 

If the area keeps appreciating, you could refinance and reinvest that cash in another property, then repeat several years later after you've built up more equity.If you can take the proceeds of a sale and put it toward a better property, then it makes sense to sell.