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My personal situation:
Almost 49 yrs old, wife 47, 2 kids 14 & 18
No personal debt, own home, own our own business, about 300k/yr income
Cash investments about 1.75 mil
Property values about 1 to 1.25 mil
Can expect to invest about 15k/mo until I sell the business or let the kids take it over in about 5 yrs
If the kids take over, I'd still make 5k/mo or sell it and bank maybe 600k after taxes, hopefully.
Over 25 yrs military and possess the coveted 20-yr letter, so retirement is in the bag, but I won't collect that until 60.

I'm trying to convince myself to retire from the reserves. Staying in would net about 275K for another 5 yrs service (about 470 days work) considering all future benefits and pay.
There will be an inevitable deployment next year sending me away from family for another year, delaying progress in our real estate investments and business improvements.
Retiring from the reserves would mean I'd have to pay an additional $10k/yr in health care expenses if I continue with Tricare Retiree. I haven't explored civilian health care through the business which could be a write off resulting in less overall expense, but I doubt it.

I'm trying to decide if this whole retirement thing is in the bag and doesn't require me to risk my life on another deployment. Can I tolerate the additional yearly health care coverage costs? Or is it silly to leave $275K on the table for only one more deployment and a total of 470 days work?

Go ahead, tear it up! I'm not comparing to others for any other reason than to determine if I'm in the position to walk away from 31 yrs of service. Should I finally cut cord? Thanks for your help, Fools!

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