one who brought some meaning back into his life

Word.

I agree he doesn't seem to remember what the meaning of life is to that point; and they touch on it within that conversation. "Activity suggests a life filled with purpose", "running away from memories?", "searching for a reason to stay". Elsa's his rebound girl, after the ultimate heartbreak. She was never going to be the next Mrs. Captain Baron von Trapp. 

Maybe "meaning" in the way she brought 'life' back to him.
He had distanced himself from his children and the life he led with Agathe. He must have had some meaning in that. When his wife died he lost the music, playing around, going to dinner parties., etc. I'm sure he had some fun activities while Agathe lived and now he misses them. He just can't face to do these things with his children because they remind him of his 'old' life.

Then there's Elsa who showed him there is still a world out there that is very much alive. And gives new 'meaning'

I think it would be useful to know when he stopped being a naval commander (apparently Austria lost its only seabord in the first WW, so overnight he would have lost his livelihood). This doesn't tally well with our film, but I always imagine that, if it were in the 1930s, losing the Navy and his wife would make him fall into a dark depression, losing interest in everything including his children and going nowhere.

So you can see how meeting Elsa, and feeling that spark of excitement and fun again 'brought some meaning back to his life', as well as joining in with the ready-made social life that a woman like Elsa would have offered him (hence the trips to Vienna). In terms of how long he has known her - not longer than a year, I think, because they don't really know each other all that well! Yet it might be a time when they would be thinking about marriage.

I always liked stories that had her know agatha too. It kind of adds to the presumption that they should marry because they have so much in common. She could remind him of agatha maybe.

IRL he inherited Agathe's vast wealth. Some stories have him doing contract/consulting work for the British Navy, engineering work, stuff like that. Independent, so that he is free to go off to Vienna for weeks as a time. No 9 to 5 desk job for our man.

And what are Georg& max?

"Max" is based upon Father Franz Wasner, a missionary, who was conductor and director of the Trapp Family Singers. He and Georg were close friends. I suppose Max and Georg are, too though I've read some fics where they are cousins.

although, I like charleybec's answer better. 

and going out riding with the riding crop.....

that is cool. how did you find that?

google. i got 'vega shipping company' from the book.

The timeline is totally different in the real story than in the film. I prefer to roam into the imaginary story and not in the real one. In our film I guess that his wife died when little Gretl was born, that is 5 years ago let's say. I prefer to imagine that until then or maybe 1-2 years after he continued working because we see him totally absorbed by giving orders to his children that present themselves by marching. He distanced himself from his children, obviously felt emotional numbness and this numbness is what he tried to cover by going to Vienna and partying with the Baroness. She made him feel relaxed and have a good time I think. They had common circles and friends, they went to receptions together, travelling, vacations etc. But he still remained a riddle as the baroness said. He had not found yet peace...