robho - 8:51 pm on Nov 5, 2010 (gmt 0)

FWIW, my top four sites (for both traffic and income) have 9, 9, 11 and 12 letters in the name, so I think shortcuts are over-rated. Facebook does OK also, compared to the shorter bebo...

Does the acronym pass the radio test? Can you say it out loud easier and faster than the existing name?

Tax-wise I believe most countries treat the odd sale of a domain name as a capital gain (sale of a capital asset), unless you're in the business of buying/selling names when it becomes trading income. But check for your exact situation.

However, if the money's not enough for you, it's not enough.

Calculate in how much time you will divert from earning real money, as well as the lost business from changing the name. For a real business with products you'd also need to change labels, invoices, ...

In other words, it REALLY has to be worth your while for the hassle, or you have to have a real need for a short term injection of cash.