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Sam Handwerger from hcfandl.com did my taxes this year. I can't recommend him enough. Getting advice from the forum is great, but I can't stress enough how important it is to have a quality accountant. Pays for itself 100 times over.
Also, many people are afraid to ask their accountants about tax avoidance strategies. There is really no shame in it, and anyone who makes real money from domains should be at least looking at these options.
Man Rock, I don't envy your nut to the tax man this year, but I don't see you making any fire sales.
Not a gray area at all. If you write it off as inventory you need to devalue it each year but that's not easy to do with domains (unlike, say, homes).
But as Rockefeller said, if your purchases were made with a company formation in mind, then it can be deductible.
I treat all my purchases and acquisitions as long term cost, to be deducted upon selling them. Monetization (e.g. via parking) has nothing to do with taxation of sales; it's regular revenue.