I've been a Weber kettle cooker for years, and when the time came to either refurbish my old 22" or upgrade, I elected to go big.  You don't really appreciate just how much more flexible a 40% increase in cooking grate area is until you use it.  I'm able to cook three big steaks, six ears of corn, and a pan of sauce or veggies all at once without the arrangement getting cumbersome.  I mainly use a direct/indirect setup - if you're used to doing it on a smaller grill, there's practically no learning curve involved with moving over to the 26".  My only recommended change is to at least offer the Gourmet Barbecue System grate as an accessory - it's the only way I feel that I'm missing out on anything.