There's not a lot to it. We've organised our own trips for the last few years. Check back through this forum using relevant keywords and you should find some usefull links.
There is *no* big deal to getting lift passes. You go to the lift station on the day you arrive, buy the pass, go home. Prices are clear and the process is transparent. Lift companies depend on things going smoothly given the volume of people they process so it is in their interests to make it simple with big clear signs showing prices and details. Unless you are somewhere particularly strange then almost everyone working in the resort will have some English - again it is in their interests in terms of getting business.
Contact the tourist information centre for the resort you are thinking of and they will be able to provide a short list of accommodation available for the period you are thinking of - saves a lot of time ringing and emailing hotels directly.
Ski classes are (again) geared up to getting people in with a minimum of fuss, so they all speak English and in our experience the prices are pretty much constant between different schools so there is little point in shopping around. Some of them will provide discounted ski hire when you book lessons.
In terms of train access, it couldn't be much simpler. This is Europe we are talking about - not Ireland. Trains run on time. Trains go where they are needed. Trains are good value. A quick look at a map of Austria shows a train line running across the country from the pointy bit in the West through St Anton, Innsbruck, Kitzbuhel, St Johann-in-Tirol, Zell am Zee and Salzburg. Branches off this line go to Mayrhofen, Zell am Ziller, Obergurgl and a load of other resorts. Munich has good links through the Alps to this line as well as Salzburg & Innsbruck airports. One important thing - these trains are very busy on Saturdays as everyone arrives, so be sure to book tickets & seats.
Enjoy.
z