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I have a very large unrealized loss in one of my stocks(outside a retirement account). I purchased an equal number of shares over 31 days ago with the notion that I would sell my original shares while maintaining a position in a company I really believe in. However, I am wondering if it is worth it to realize the loss now as I don't immediately have capital gains to offset that are nearly as large as the loss (i.e. my current capital gains are much smaller than the loss I am about to incur).

I have several questions:
1) What are the limitations to carrying over losses into future years (i.e. time limit if I don't use it all in the next few years or monetary limit)?

2) Am I correct in the thought that I can use capital losses to offset only $3000 in earned income in any year? If so, would I just be carrying over my loss to predominantly offset future capital gains then?

3) A couple of years ago I converted an IRA to a Roth IRA. Doing so, I incurred a sizeable tax liability (still smaller than the current loss I am talking about) which I was able to spread across 4 years. I already paid last year and have paid this year. Can I use my loss to a) offset the next two years liabilities and b) get a refund of the IRA conversion taxes I paid last year and this year?

Any input will be greatly appreciated.

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