... Or tell me if you think that this is impossible!
I am relatively inexperienced with SolidWorks so I am not even sure if the option described above is even available!
Welcome to the forum. Other than basic colors and Material I don't use Appearances much, but I'll try to help. As far as your company library wood grains, you can add those to the default appearances. Go to the Appearances tab and choose the Add File Location icon.
Then browse to the folder where you have the files stored. That folder will be added at the bottom. I have added decals on mine.
I believe that will take care of your question #1. For question #2, as I said above I rarely use these, but I doubt that you can get them to automatically orient correctly. Hopefully someone else will respond and correct me.
I use a lot of different laminates on parts that I create at work. What I have done is put the laminates as a jpeg in a folder and when I need them I open the folder and left click on it and drag it to the part I need the laminate color on. Then i left click on it and click on the appearance down button then click on the face that you applied the jpeg to(it will have the "x" next to it), after this over on the left you will see default texture with 2 buttons, basic & advance, click on advance and the click on mapping. Down below you will see size/orientation, click on fit width or fit height to get everything sized correctly. You can also rotate the jpeg to get the grain direction going the right way.
Hope this helps.