Try not to beat yourself up. It's so tough to know the right thing to do in those situations—especially since you were younger when you were faced with the decision and information was sparse. My SIL worked as an auditor for the IRS for decades and when she left her job to move to Sedona, AZ in 1995 she was faced with the option of a lump sum payout that greatly reduced her Social Security payments when the time came for her to collect it. She was in need of $$ at the time, for the move, so she took the lump sum payout. Now her SS payment is now only around $300 per month, not nearly enough to live on.

The price of private healthcare was the main thing holding me back from leaving my day job so long, especially before the Affordable Care Act was put into place. Healthcare costs are high atop of the list of things I continue to worry about as well. My wife will be eligible for Medicare in a couple of years and then I'll have to stay on UCare for another seven years. UCare so expensive, even with income subsidies, as well as being very complicated to navigate. The past two years in a row we've been kicked off the program due to "clerical errors", put on county assistance which made us lose access to most of my wife's specialists, and had to spend countless hours getting things straightened out. Our healthcare system is so broken, there are so many layers of bureaucracy it makes your head spin. We desperately need universal healthcare in the US.