Obi-Wan Kenobi is one of my favourite characters in the entire Star Wars franchise. As a kid I loved the wisdom and guidance he gave to Luke and in the prequels and Clone Wars it just built up to make a really rounded character arc.
Ewan McGregor has done a great job playing him in the movies and has some of the most memorable lines and guidance in the entire trilogy. The Clone Wars Kenobi built upon the character and added complexity, more tidbits of wisdom and a look at his own struggles with the Jedi way of living (see Mandalorian episodes of the clone wars for reference).
Now we are facing a Kenobi Disney+ series with some of the original cast and it's got massive potential, especially looking at where they went with the end of season 2 of The Mandalorian i.e nothing is out of bounds.
So the timeline is going to pick up 10 years after the events of Order 66. Luke is going to be 10 years old and living on the Lars Homestead, Obi-Wan will be at a distance living in his hut that you see in A New Hope and I have to imagine that we'll see him jetting off Tatooine and slowly coming to terms with the events of Revenge of the Sith. Given that we are seeing both Ewan McGregor and Hayden Christensen return to their roles then surely we will see him meeting Vader, the first meeting. We might also see some Clone Wars flashbacks, that would be a great tie-in to the animated series.
I really think this is going to be a pretty dark series with Obi-Wan dealing with a lot of negative emotions, thinking about the past and protecting Luke from the Empire. He doesn't get on with Luke's uncle at this point who wants him to keep his distance and leave Luke alone to prevent him taking the same path that Anakin did, following Obi-Wan into the Clone Wars.
Could we see some surprises? - yes! Mandalorian showed us that these surprises can happen and would be welcome. Personally I'd love to see
A 10 year old Luke, maybe just at a distance or a chance encounter but not a character in the series
Qui-Gon as a force ghost once Obi-Wan masters the home work that Yoda gives him at the end of Episode III
Yoda - I have to think he'll be there at some point as a guide to Obi-Wan
Ahsoka - Would be a great little cameo and I'd love to see a talk between her and Obi-Wan about the fall of Anakin. Doesn't need to be an entire episode but I love the thought that Ahsoka knows what happened since the fall and the events from the other side of her encounters in the Clone Wars (final season), you really do need to watch the end of the Clone Wars to get the entire picture here
What are you hoping to see from the Kenobi series?