I'm considering a TB bag as a Christmas gift for a friend, who already has a Checkpoint Flyer, which is well-liked. The only complaints about the CF are there's not enough separated organization zones/pockets and it's a too large for "in the office days". Right now, the CF is used only for travel days- the reason I thought second TB bag might be appreciated. My friend adores bags with a vertical orientation, so I thought a Cafe or Ristretto bag might be a good option. Two items my friend must have on hand every day - an iPad2 and a leather portfolio with a letter-sized (8.5"x11") writing pad. I'm guessing the portfolio is 10"x13"; I can't confirm exact size without raising suspicions. Sometimes the portfolio is replaced with a Levenger Circa notebook; that's also letter-sized and a bit larger than 8.5"x11". Other contents would be the usual - phone, pens and pencils, wallet, lip balm, earphones, and maybe a charger and sync cable. I'd be willing to get larger Ristretto - it would still hold iPad2 and allow for future upgrade to MacBook Air or Pro - if it would hold a portfolio.
My question is...Are any of the Cafe or Ristretto bags large enough to hold a letter-sized portfolio or Circa? Without making the flap look like it's lifting? I tried searching the forum, but didn't have much luck. My search skills need work.