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Can someone tell me how much of an investment loss I can deduct from my future gains (long term) for tax purposes?

Short term losses go against short term gains. Long term losses go against long term gains. The total short term gain or loss is then added to the long term gain or loss. If there's still a loss, $3,000 of the total ending loss can go against ordinary income. Unused amounts above that are carried forward indefinitely. The only limitation is the $3000.

And how long before I can re-invest in the same company?

You mean if you sell stock for a loss? You have to wait 30 days after the day of sale. You can buy on the 31st day. The 30 days doesn't count the day of sale.

I am still hoping that the original value of my shares climbs back up and approaches their 52-week high. This way, I could hire a financial advisor to re-distribute my very, very narrowly invested portfolio (a minimum of 100K is needed to hire one). So for now, I am looking for ways to minimize my tax burden.
Any links would be greatly appreciated too.

This is the IRS publication web site.
Download Publications 17 and 550

By the way, don't sell just to use up the tax loss. You save the most by having only losses and letting it net against salary.

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