I'm guessing you're flying in/out of Geneva with that second week in Bern. You know our official advice. Rent a car for the entire two weeks. Decide where the first week is based upon weather forecasts/snow conditions a week or so in advance.
I can't imagine why not. The Classic Route is very intermediate. In fact, you and your son might investigate a guide that would take you on one of the Envers du Plan routes through some icefalls. But for someone who goes to the Alps rarely, I'd say don't pick Chamonix for a week until that upper Grands Montets tram gets rebuilt.
You can't count on any off piste being available that early in the season. But if it's a good year like Liz and I experienced in 2014 we would recommend highly.
St. Moritz profile is somewhat like Zermatt's but not quite so rocky. Our visit was late January but in 2019 which was a big year for the Graubunden region.
Late January is a high probability bet for the Arlberg, and I don't think that was the region of Austria jimk visited before. Again, with these visits being rare it seems logical to go for one of the best. Val d'Isere/Tignes should always be on the short list with that in mind.
The only Olympic events in the Dolomites are in Cortina. The Sella Ronda resorts should be business as usual (we liked Arabba as the base). If your wife is an intermediate skier, the Dolomites are a great choice cruising around that amazing scenery with high quality dining options. If she does not ski at all, you should aim for a destination best for you and your son. Thus my recommendations of the Arlberg and Val d'Isere, both of which have nice resort towns too. But I would still wait until close to departure time to commit any lodging $$$.
Recall that day tickets in the Alps are in the $75 range. Thus choice of resort should not be constrained by your season pass like it might be in North America. That said, you could easily spend a week or more in the Aosta resorts if snow is decent.
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