In my mind the Newport has become synonymous with the Keen brand. When someone tells me they have some Keens or are getting some Keens this is what I think of. I've owned mine (Bison, size 10 1/2) for a year now and I've never once regretted my purchase.
Like any good shoe they've only become more comfortable as I've worn them. The initial fit was a little off from what I was hoping for but with some wearing in they feel great.
I've walked around town, stepped around the deck of a sailboat, done some small bike rides in them, worn them in a couple of inches of dry snow (with socks) and haven't had any problems with their performance. The option of wearing them comfortably with socks provides some more variety that really makes them more valuable than sandals where socks are not a plausible option.
So far they have been durable although I haven't put them through any extremely abusive situations yet although I feel they will be able to stand true when the time comes. The leather may require some care in the future but having to care for a product to reap exceptional longevity is no con in my book.
As far as "look" I personally like the look of the Newport's leather more than the H2's nylon. The leather provides that classic look and gives the wearer some options to transcend the "outdoorsy" look when desired. With the Bison color I'm even able to wear some brown socks under them and not feel ridiculous in situations where I'm dress casual. Also, other reviewers also seem to attest to the superiority of the leather over the H2's nylon as far as longevity though I'm sure there are two contesting schools of thought on this.
What makes the Newport's a great purchase is that, if you come in with reasonable expectations, you get what you expect to get-- and maybe even a little more.