Dick Watson <littlegreengecko[at]mind-enufalready-spring.com> wrote:

- quote -

The advantage of taking company stock as stock is you get to
use the NUA (Net Unrealized Appreciation) as listed on the
form 1099-R as long-term gain rather than ordinary income.

--
Art Kamlet ArtKamlet [at] AOL.com Columbus OH K2PZH

<< ================================================== ===== > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2006) - All rights reserved. > << ================================================== ===== >

I can take part of my rollover in "equivalent whole shares"
of my previous employer's company stock in which my basis is
about 50% of the current price.

My understanding, which I'd like a second opinion on, is
that I can walk with this stock, put it in a regular
brokerage account and:

1) Have to pay taxes on the basis this year as ordinary
income. There's no withholding, so I have to either goose up
my W4 withholding and/or file some 1040ES payments to avoid
penalties next spring.

2) Lock in all of the rest of the gain as unrealized long
term capital gain taxable at the investor-preferred rate.

3) Have the purchase date, for purposes of considering any
**future** gains/losses in these shares as short- or
long-term, set at the date of the rollover transaction.

4) I'd have to start paying taxes on, presumably, qualified,
dividends while I hold the shares and they keep paying the
dividend.

If I go this route, one year from the rollover, ALL capital
gains over the basis can be realized and treated as
long-term capital gains.

Does this sound right?

<< ================================================== ===== > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2006) - All rights reserved. > << ================================================== ===== >