Deciding on Health Insurance pay now or later

It's that time of year to decide if I try to save money on monthly health cost and roll the dice that we have a healthy year or higher premium with less out of pocket max.

It's a no brainier to go with a plan the has a Health Savings Account (HSA).  For the first time this year I have a chose between two plans. 

First what is a plan that has an HSA. First off the plan has to meet certain criteria to be eligible for HSA contributions. It needs to be a high deductible than a traditional insurance plan (year 2020 - min 1,400 for individual and 2,800 for families, Max single 6,900 and family 13,800) and also your employer has enable the plan to be eligible for being a high deductible plan (HDHP).  Some benefits are that the monthly premium is usually lower, but you pay more health care costs yourself before the insurance company starts to pay its share (your deductible). 

Why an HSA?
An HSA allows you to pay for certain medical expenses with money free from federal taxes.  HSA contributions are tax free going in, tax free growth, and tax free going out as long as you use on qualifying medical expenses.  For 2019 max is 3,500 single 7,000 family and next year 3,600/7,200

I've been dumb for many years and just learned of the magic of an HSA last year.  My family of four is healthy, but the kids are in school so lots of germs. Most of our doctors visits are wellness and sore throats. I would say we spend maybe a few thousand on medical a year.  I know many people may need the money they contribute for medical expense in their HSA. I'm planning on using it as another retirement account.  I'm keeping track of all medical expense in a spreed sheet with date of visit and cost.  That way in the future when I need the money for an emergency or for retirement I can reimburse my old medical expenses.  Win win for me.

My wife and I currently work for the same company so are benefits are the same.  Depending on the plan it is sometimes cheaper to have our own insurance vs whole family.  I'm currently trying to decide if I should be on my own plan because one I don't really get sick and two as a male if I do get sick I would rather die then go to the doctor (😷). Obviously not really true, but it is true enough for most guys until they get above 40.  Probably a reason women seem to live longer. Anyway if I get my own plan the wife and kids will overall have a lower max out-of-pocket even though the now combined out-of-pocket is slightly more then if we all had the same plan.  Really it only saves us about $200 off the yearly cost of the plan it would be more for the plan deductibles.  

Who knows I have about two weeks to decide how healthy we will be next year.  I will try my best to try to play this scam that is health insurance.  

Good luck and let your choices forever be in your favor.