Nice, man. Looking forward to some pics of the tassel loafers once you wear them in!
Re: that bag, I'd be inclined to save a bit longer and spend on a Filson bag as that's a blatant copy of one. Gerry has the Filson if I'm not mistaken, and at the risk of speaking for someone else, I think he'd feel the same. With an item that gets as much use as a daily bag, it's best to spend more once off than replace it every 10-12 months, IMO.
When you have nice bag, you make big smile.
TBM said it very well. I enjoy my Filson everytime I use it. It constantly surprises me at how much it's able to store without looking stuffed and the canvas is getting softer as time goes by. As far as a briefcase goes, it's no SAB or Glaser but it suits my purposes perfectly and just gets better the more I use it.