Considering that the Wii has yet to see its first price cut due to demand, now's the best time to sell one while demand generally still outstrips supply. That's for those who care about resell value anyway.
If you've already been through the current catalog of games (and you have personally bought many of what most consider the best the Wii has to offer), and there's nothing on the horizon you feel compelled to buy, there really isn't any reason to keep it.
Not everyone feels compelled to compulsively keep playing Kart and Brawl indefinitely.
You can ALWAYS buy another one down the line when they're cheaper. Wait a couple years, and you'll probably be able to pick one up for $150 or less.
IMO, it's more trouble than it's worth to sell and buy a console more than once unless someone makes a ridiculous offer on something you weren't using anyway.
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