This is another What would you do? scenario, but I value the insight here so let me put this out there.
There is an opportunity to join a firm on a contractual basis. It would mean leaving the comfy confines of government economic development and housing, but it would come with a 20K raise. There would be no benefits (medical, dental, vision, disability, life insurance, pension etc.) with the job so those would have to be paid out of pocket. While I cannot say for sure, the workload could actually be less (weird). Night meetings would be about the same and there is relatively no impact from a distance driving to the office perspective.
What would you do? Or, more importantly, what concerns would you have? I have some idea how much medical insurance would cost, but it still seems like a decent size risk.