IMO, given all that you are dealing with, try not to worry about 2022 right now. Since you are unemployed, have you checked out your Obama care options (perhaps there is a low cost plan available) for 2021? I am guessing that we are in open enrollment still plus, when your insurance ends--you are automatically in an open enrollment period for about two months no matter what time of year it is. Also, what is the penalty for having a break in your healthcare coverage? When we used to have an Obama care penalty--I found it cheaper to pay the penalty than to have insurance because the penalty was based on our income (a certain percent of our income and if we didn't have coverage for 3 months, we would only pay 3/12s of the penalty). Getting a $60. an hour job can solve a lot of problems. I have experience with this because my husband is also in the IT field (pays well) but has been doing mostly contract jobs for more than a decade. We have been go from making it just fine to pauper status for decades--it is stressful but you adjust. We save money when times are good to get through the bad times. I also have mostly had contract jobs for more than a decade but mine never pay as well as my husbands. Contract jobs ARE less stressful--usually, they can't make you work overtime unless they pay you time and a half so, when overtime is required--contracters make great money! There is one job I have been doing every Spring that I love and I find that the fact that I doesn't last all year makes it seem fresh and less boring--about the time it is feeling a bit routine, the season is over. With contract jobs, if you are unhappy with someone you are working with--you know it will not last forever, you can just walk away when the contract ends and their is no black mark on your record--the explanation in an employment application is that the job was temporary and the contract ended.