First we recommend you stop drinking long before you risk knocking your glass over as that is just a sinful waste of good wine. (We assume it is good wine if you have a Westie Bag). Next, don't panic. You can wipe your Westie bag clean with a damp cloth. Or panic and get someone else to wipe your Westie Bag clean with a damp cloth and switch wine glasses while they are not looking.
We don't know but it sounds like a good idea and we suggest you contact the people who do that kind of work. Might be hard to maneuver the bag under the machine. We're pretty sure you can glue a patch to the bags. Try some craft glue like E6000.
You need to check the dimensions of your computer but in general they fit in Portfolio Bags and Messenger Bags as well as the Laptop Bag. Of course the Laptop Bag has been designed for them but the other bags are great alternatives.
A lot of women use messengers bags these days as a diaper bag as unlike most diaper bag totes, these are hands free yet the contents are easily accessible. Alternatively there is the bagpack. You can buy great diaper bag inserts to go with the messenger bag such as Mckenzie Kids Diaper Bag Essentials.
Sure. The bag meets the size guideline of on board luggage and fits neatly into overhead lockers. Just watch the weight - most airlines have weight limits.