I will say upfront that I travel less than your friend (I'll do ~60K/year, over the past 3 years), but during that time I have used my Orvis Bullhide Briefcase with great success. I need to use a larger profile laptop for my job, and the laptop area fits that and a leather binder with no problem. The accessory area carries everything I need, and can fit a small umbrella or flip flops into the side pouch when needed. I like the fact that it holds everything I need for business travel, but doesn't look like it's an extra-sized briefcase.

In terms of durability, this bag has weathered very well for my travel needs. I've had no strap failures or tears, and leather conditioner takes care of associated nicks and scratches. Some people also like the 'worn' look with the bullhide, but I prefer mine to look like a well oiled baseball mitt. It definitely is not a more modern look, but I personally like the comfortable yet rugged look of the bag; I tend to be more tweed-and-leather in any case.

Here is the luggage warranty:
"Our Luggage Warranty
We warranty our luggage for as long as you own it. We’ll cover all manufacturing materials or defects at no charge to you. Returned luggage should be sent to our Gokey facility for evaluation. If the luggage is not repairable, we’ll give you a call to discuss possible options. We do assess a flat $30 fee to cover shipping and handling. Please note that our warranty does not cover airline damage. If the luggage is damaged by an airline, you should file a claim with the airline."