Aha, the 'is it time to bail out & will I be OK' question!

From your brief review, it sounds as if the econ side is covered, in terms of your current needs and spending habits. And, you have another ~3yrs worth of income building/stashing, as I assume you are/will continue to work for another 3 yrs.

The part time idea from ~56 to ~62 is also good, though unless it is nailed down it may change or evolve, during the next few years.

The question of SS at 62ish vs 65, 66 or older, consumes Terabytes of storage on the net; fwiw, most of my Geezer buds all took it at 62, as none of us knows when we are checking out. The only ones that did not take SS at 62 were still employed, consulting, etc.

The health insurance issue is mainly a question of how well you are currently covered, and if any of your current plan would slide over, (other than COBRA), if you bailed at 56. I bailed at 53 in 2000, and we paid significant dough every year for BC/BS with a $5G major medical deductible. Didn't miss lunch because of the $6-$8Gs a year for our 'coverage', but it is a cost off the top or bottom. I hit Medicare last year, so our ins cost is down to $1300 a yr for me and $5Gs a yr for my CEO. But, health care costs are high, going higher by the day, and nearly unconscionable in this country, imo.

The med ins/cost/future cost is the only really vague part of your brief review...

I couldn't take another fookin day when I resigned; you may come to feel you want to work longer, a different gig, a less stressful gig, or that part time routine. My point is my CEO and I both had very good jobs, big dual income and saved like squirrels. But when we both walked early, the income stream came to a screeching halt after my resign contract was up. But, we were fed fookin up, with our careers...and 'part time' wasn't really a possibility for us.

13 yrs later, we are still fine/solid with a good sized portfolio, 2 houses, etc. But, it has taken careful planning, careful self directed investing, some luck and not getting sucked into boats, F Cars, et al.

The only surprises were 'adjustment', as in I used to be in charge of a $ Qtr Billion operation with a couple hundred people and suddenly I was 'in charge' of no one, esp the Boss of the house. And, there were some boring days along the way, even with lots of hobbies and activities...

Personally, I would do very little differently, and I am glad I have had these past 13 yrs as a RetiredBum. Hope to make another healthy 10, but as you know, none of us fookin know when our expiration date is up.

You have a good handle on your projections, but the med ins cost for the next few yrs , and then post job is a bit sketchy, (and maybe none of my biz), but Medicare is a long way off for you.

25 yr roof?! Now that is thinking optimistically!
My 50Cts...
Best Regards, mD

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Ol'UncleMotor
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The pt is rather easy for me, I have only worked about 9-10 months a year for the past ten, getting it down to 2-3 is just a matter of selecting the right jobs at the right time.

SS at 62 is so much lower than at 67 or 70 so I am not really counting on it... I'm thinking I will just spend from my savings at least until 67. Collecting SS starting at 70 would itself carry me so it is very tempted to wait till then. I am also thinking though that if the worst happened and I ended up living off the SS promised, I could also reverse mortgage the house to have a little extra. I'll have to look into whether or not I qualify.

This is the big unknown anyway you look at it. It can totally derail retirement if you get sick and must be feared (or at least worried about), but not really anything you can do about it.

I took 10 months off this year to see how the numbers would flow. I am happy to see that my numbers went forward - instead of in reverse. But this has been a great year for the stock market. But being cautious is why I plan to still work fulltime for the next three years.

I have plenty of personal (hopefully money making) projects on-line that should keep me from getting too bored, but to paraphrase you, "being free will be fooking worth it."

Thanks for your input.

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2006 X5 Sport 4.4i

buy property in Panama, transfer your monthly payouts there, get pensionado visa, import tax free household goods, car (tax free once every two years), buy into local medical coverage (excellent hospitals, on par, if not better than the US facillities, US trained docs), US currency (no exchange), most folks are fluent in english, major international port and air hub (under $300 round trip to US), super cheap living on the oceanside, rare hurricanes (they pass further up north), a lot of tax-free perks, the roads are built by US Corps of Engineers......
do not go to costa rica (too expensive), or nicaragua or belize (too poor, even though cost of living is low).
or, Philippines, as another alternative to panama...

I've thought many times about becoming an Ex-Pat... But for now I think I want to stay at home.

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2006 X5 Sport 4.4i

Divorce.

53 here. At a crossroads, thinking I will just retire now. Because I can, I guess.

To MD's excellent comments, I would just stress the health care cost. I agree that we can't do much about getting sick, apart from living healthy to improve the odds. But don't just plan for the best. I would hope for the best, and plan for the worst. Being sick, especially over an extended period, is very expensive.

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2007 X3 3.0si, 6 MT, Premium, White

Retired:
2008 535i, 6 MT, M Sport, Premium, Space Grey
2003 X5 3.0 Steptronic, Premium, Titanium Silver
2002 325xi 5 MT, Steel Grey
2004 Z4 3.0 Premium, Sport, SMG, Maldives Blue

Not an issue.

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2006 X5 Sport 4.4i

I guess the only thing left to do is to go ahead and get the airplane built, and then drop out!

Good luck to us all as far as health goes.

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2006 X5 Sport 4.4i

At 72 years old completely. Life is based on health weather you live
in a mansion or in a trailer. Remember bad decisions regarding health or
your health care plan will affect everyone in your family. JCL is right.
Plan well and live healthy. The quality of your retirement depends on it.

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Harmony happens whenever different parts get to form a whole by means of congruity, concord, symetry, consistency, conformity, correspondence, agreement, accord, unity, consonance…….