"I've had this bag for almost exactly a year now, during my first year in business school and over the Summer. I use the heck out of this bag, literally every day, to carry my laptop, cords, and usually at least 20 pounds of books, files, folders and electronics all over the country and campus. It has been attached to my hip for 1 year, so here are my thoughts:
Construction and the leather materials of the bag are great. The shell of the bag should outlast me easily.
Like others have mentioned, the nylon dividers and pockets are floppy and catch on the corners of media I'm putting into it. I think the nylon used is durable, and for the most part stitched well, but stiffer compartment dividers with pockets that are flush with them would suit me better for ease of inserting files, folders, books and all the stuff I previously mentioned.
I accidentally bought an extra strap for the bag, because I didn't see that it came with one in the description. I'm glad I did, because the original has stretched over 1 foot (that's my fault most likely-I carry a LOT of books and equipment in it.) But also the cloth/rubber strap pad has worn through and has about a 3-1/2" tear in the edge of it. That's from daily use for 1 year.
I take very good care of this bag, incidentally, as far as cleaning and oiling it. Like another reviewer, I don't particularly like the giant 'Orvis' badge on the side, but hopefully as it ages, it will become more indiscreet. One of the main reasons I shop at Orvis is that their branding and logos are usually subtle, compared to other brands I used to buy frequently. As an MBA student concentrating in Marketing Strategy, I'll offer that Orvis has several unique customer bases, and the one that contains the people that would buy this product aren't the customers that are looking to pay premium prices to advertise the manufacturer or where they bought it, such as fly-fishing gear or any battenkill product. This affluent segment will pay extra for subtlety and tradition. This is a word of mouth/legacy product, and I have successfully convinced two classmates to buy one as well.
I wonder what's going to become of the velcro strap that holds the laptop in place. The elastic strap is already becoming sort of shot, and the stickiness of the velcro won't last as long as the bag. Also, the velcro tab scarifies the nylon when not attached. But I'll cross those bridges later.
The only other "complaint" is that the stitching has come out above the 'Orvis' tag inside the bag. I didn't do that; it was an inspection oversight, but minor.
It's a diverse product, in that I think it would be fine to take in to a business meeting and is casual and rugged enough for everyday use, and is very handsome. People notice this bag wherever I take it (which is everywhere, and may be because I have so much stuff packed into it ;))
Overall I'm highly pleased; this bag has exceeded some of my expectations, and fallen a little short on others, but for the money and the demands I have placed on it I consider it a real value, and hopefully it'll be around for many, many years to come. I'd recommend buying an extra strap or two just in case, since this bag will most likely be in your family for generations."