BPickerCPA

Annual contributions come out first, conversions come out next, in order of the conversion, income comes out last. Every time you make another annual contribution, that goes to the "head of the line".

No. The recharacterization is irrevocable.

When I converted my son's IRA to a Roth at Schwab, all that happened was that the assets ended up in a different account with a new number. No fee, no commission, and it took no more than a few minutes. Can't speak for other brokers, but it sounds like you're getting a story. If you heard this from a broker, go up the chain to a supervisor or beyond.

Income from a conversion is NOT included in MAGI for purposes of the contribution limit.

You CANNOT convert an inherited IRA. What a spouse can do however, is to treat the IRA as her/his own, and then that IRA can be converted. If the spouse died in '98, and the required distributions will be over $100K, then it looks like '98 is the only year you can convert it to a Roth. But it MUST be put into the survivors own IRA first.

Yes, as long as your income does not exceed the limits for Roth contribution.

Only if your child has EARNED income. HIghly doubtful, unless he/she is doing some modeling or acting.

You can do transfer of a 401(k) into a traditional IRA and then into a Roth. You cannot transfer after tax money into an IRA or into a Roth.

It sounds like you have it figured correctly. Of course, keep in mind that the income from the conversion is on top of your other income, and could push you into a higher bracket. But breaking up a conversion to stay in lower tax brackets is a great planning technique. Obviously, with no knowledge of your entire situation, I can't speak of the advisability of converting vs not converting.

Yes. You have until the extended due date of the tax return to do a recharacterization.

If the four year spread is used, then it's four years, equal reporting of income (unless a withdrawal is taken, but that's a different story). If the taxpayer dies and the spouse does not inherit the Roth, then the remaining income is reported for the year of death.

Cap gains ARE included, tax exempt interest income is NOT.

Unless it is a rollover contribution, which you indicate yours is NOT, ONLY CASH is allowed.

Yes, as long as you're within the income limits for a Roth contribution. You mention a '99 contribution. If eligible, try a '98 contribution.

That question, a crucial one, still has not been answered by the IRS. The best I can get from them is that they will take each case on an individual basis. I interpret that to mean that if they feel the error is grievous, they will sock the taxpayer. If it's a minor miscalculation, they will be lenient. In truth, the law, as it is written, does not permit late recharacterizations. I think that Congress may have to get involved, via a law change.

You have 60 days to roll over a distribution back into a Roth IRA. After that, the money cannot go back. You can always put $2K of new money into a Roth, as long as your income does not exceed the limits.