I believe they expect us to rollover and let our insurance company handle it and just settle.

Rollover risk would make me have some reservations but we would need more details 

I have my HSA, my roll over IRA, and an account I keep there for emergency funds.

Ensure your investment pipeline justifies the fees, and consult the custodian about rollover options to avoid unnecessary expenses if investments slow.This post does not create a CPA-Client relationship.

@Tessa Mac You can certainly rollover your old 403b plan into a self-directed account. 

First you will have to ensure your 401K is eligible for roll over to a SDIRA.

You only roll over the 2mm, take a 500k cash out and then claim the 500k sec 121 exemption.You can think of it like taking the 500k off the top, then the remainder functions as a normal 1031 exchange would.

Or maybe they offer the option to roll over and stay in it, if they were able to add value, increase cashflow, etc., making the long term return is favorable?

@Jacob CampbellMy understanding is you cannot sell your relinquished property and roll over proceeds into a property you own to payoff debt. 

‘The real estate brokerage industry in the United States is all about making the process of transacting real estate “frictionless”.