Re: Timelines
Well, the "surely he must be dead BY NOW", gives rise to the thought that Ben must be very old. What else could it be, they had no idea where he was or Vader would have tracked him down with an army and killed him. So if they didn't know where he was, they didn't know if he was living on a planet where chances for a lengthy survival are slim. And if Tarkin expected a bounty hunter to have killed him, I'm pretty sure they'd have known when the BH came to collect the bill.
So that aging stuff is something GL must be struggling with.
Personally I think the preconceived idea of ANH was roughly that OB1 was already an older Jedi, like Qui-Gon in TPM, and Anakin was the same age as Luke in ANH when he started his training with OB1 ("When I met your father he was already a great pilot", surely GL had no idea about the pod races then). That would have made a lot of sense with the aging and all. It's a little weird for Vader to call OB1 "old man" when there's only 15 years age difference.
Anyway, lots of age anomalies. In my humble perception, of course.