Ahsoka can easily show up in Obi Wan's timeline, quite possibly just before he meets Luke, and Obi Wan can easily show up in Ahsoka's as a force ghost to offer guidance and comfort.
It's gonna happen.
And don't be surprised to see Vader/Annakin popping up in all kinds of unexpected places.
There are going to be more light saber duels than you've ever seen before, and it's gonna rock!