So I stepped up to the plate and purchased the iPad Messenger Bag from Vaja ($280 + $64 shipping). I have it now, and here are my thoughts. PROS: The leather is high quality It can fit iPads with low profile covers It will be good for any iPad ever. It isn't built for one model CONS: It definitely seems like a purse. My wife now questions my sexuality, and I'm not sure I'm 100% comfortable carrying it in public. Some of this has to do with the bright red trim It's too expensive. $344 is too much It has very little space for anything else and the small pocket is just weird. Not sure what I should use it for and why they didn't make it bigger. Looking back, I probably should have gone for the Tom Bihn Ristretto. I would return the Vaja if I could, but I still haven't made up my mind. I think I'm just going to keep it until I determine whether I like it (and "man" up to it).