Like Neil, I have the Vista HCX. As he notes, it has the best battery life, really remarkable that it can run for days and days. I have the problem with the rubber coming off too. The vista has the joy stick and several small side buttons. I find using the buttons and joystick awkward while I am riding. But I don't switch screens or setups that often. But that would be its main disadvantage for riding. THe vista display is too small for auto routing if I am the driver and really don't know where I am going, but I think for auto use like that, all the handhelds would have that problem; except the Oregon, may be big enough to really see the map when driving.
I think the Oregon you link could be a great deal. The knock on the Oregon was that the display is harder to see in bright light, so you may want to check one out in person outside wearing sunglasses, and see if that works for you. My memory is that the garmin bike mount for the oregon was a cheap velco band or something like that. There are probably other ram mounts. I would guess the touchscreen would work better on the bike; not so good for wearing gloves skiing in the winter.
You may not need to buy the Garmin Navigator or any Garmin maps anymore (so the Oregon 300 if that didn't come with maps and could be otained cheaper), since in the past couple of years there has been a mass project to develop free maps for Garmin GPS, including topo maps of the the US and Canada, and now routable maps too (open street maps is that project). The routing on the vista with the open street map can be funky, and so I can't tell if that is the vista or the free map, so something that would also happen on a better unit and a commercial map.