First of all, HHotties are so helpful! Thank you.
Second, here is a photo that illustrates my concerns. The blue bag is my Urban Junket workhorse, the elephant gray one is my Linea Pelle DMT, which I carry at least a couple days each week, the you know the Corcovado!
1) My current workbag, which is great for organization and laptop protection, but is too of heavy and totally beat up, is an original Urban Junket bag. They no longer make it in leather but too make something really similar in a coated canvas. I got it for around $400, now the non-leather version is just over $100. I have carried this bag almost daily for 2 years, and it shows.
2) The Dylan Medium Tote is one of my favorite bags and is now a smooshy puddle of gooey leather. I love it, but it's seen better days. And it's not 'professional' enough to carry as a work bag when I see clients. Getting papers out of it is hilarious, since it's so broken-in. But I love this go-with-everything color, and I still use it often.
3) The Corcovado looks amazing, it's clearly built for organization, and I think it looks more put-together than either of the other bags. But is it too heavy and too small to be my 'ideal' laptop-and-papers-and-stuff bag?
I'm not convinced. I love it, but would I be better off getting a completely different (non HH) bag for work, and just getting another bag I love - a Havana Hobo or Tharpe Hobo in a color I don't home - to carry in addition to a more functional/boring laptop bag.
Or should I use the Corc for a workbag and learn not to overstuff? Or just keep it and use it as a handbag but not a daily laptop carrier. (Because you are right, the opening makes it a little tricky!)
ACK! I feel like a mess here. Thanks for listening and providing some counseling. I hope you offer reduced fees for total basket cases.