No pension, no health care here. We have been buying our own health insurance with $10K/yr deductible. Premium a bit less than $300/month, which also covers my 19-y.o. son in college. I think the following things help us.
1) Being LBYM'ers
2) Staying married for 28 years.
3) Being in the same home for 20+ yrs; no moving costs.
4) Living in a place with low cost of living, and low taxes.
5) Good income, though time off for 6 years on eventually-failing business ventures (reduced pay, then no pay, never 401k matching), followed by 6 years of sporadic consulting work (1099) + job shopping (W2) hurt. However, it prepared us for eventual "no work". Twelve years worth of "training wheels".
6) Dual income. However, my income was so sporadic the last 12 years, such that we were hit with ATM only 2 years. On the good years, also no college tuition deduction, no IRA allowed either. On lean years, the reduced taxes didn't make up for the taxes we paid in "fat years". Such was the price to pay for the privilege of not having to show face from 9 to 5.
7) Kids live at home and go to local state university, my alma mater.
8) Good health (knock on wood).
9) Always max'ed out on 401k, then IRAs or Roth whenever eligible. Could have done a lot better if, early in career, diverted time from technical and work-related self-study and research to understand investing and the stock market.
10) Being handyman around the house(s) and also being own grease monkey. Drove cars to the ground.
11) Being paranoid about running out of money. Getting better recently.
There may be some more, but that's all I can think of now.
About SS, when my portfolio kept hitting new highs despite our travels, I did not bother to look at the statements SSA sent. Who needed it?
Recently, pulled them out and entered into FIRECalc. Looks a lot better with it. So, party on.