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I plan to retire in two years at 62 (I probably won't, but I am planning that way). I am thinking to pay off my $200K mortgage at that point or shortly after. I have $500K in non-tax deferred money with long term gains to exploit. I am looking for opinions on whether to cash in the day I retire or spread it over time.

cashing in all of it, or just enough to pay off the mortgage?

either way

1) iirc, there was some "special deal" on long term cap gains last year (2010) and i this year also but not next .. so you might want to cash in now [ one of the experts will correct me ]

2) you want to spread it out At Least enough that your cap gains don't bump you into a higher bracket /make your SS taxed 'too much'

might consider looking at your tax situation late in the year and do 'what-ifs' or various amounts of cashing-in

3) if you think whatever you're selling will continue to go Up, you don't want to sell any more than you have to

[ 4) just me, but i like keeping the mortgage and having the cash in case of emergency ]

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