This is probably my last video for a month or so. Within it, I discuss the difficult chronology of Genesis 38. I’ve written a lengthy post here, which gets into some of the typology of the chapter in its context. I also mention the Judah and Tamar narrative in the context of this video on Ruth the Moabitess. Unfortunately, the sound quality is poor on this one.
Alastair's Adversaria 
Thanks Alastair for these thoughts, which add something to my understanding. If I may, I would like to add a few comments.
The real timeline problems come when we consider that 9 years into Egypt’s famine the family of Jacob all travel to Egypt and Jacob meets Pharaoh aged 130. Typically, people count backwards from there into Jacob’s trip to Paddan Aram in Genesis 28 and surmise that he was in his late 70’s when he made that trip and in his 80’s when he married Leah and Rachel. This is very old! And this is not our only problem. We have all the problems you mention (if you are right that Benjamin was not born when Joseph was sold, Jacob must have been at least 108 when he fathered Benjamin). Another problem would be that when Esau went to his uncle Ishmael and married Mahalath (Gen 28:9), her father would have been 150 – already dead, in fact. And presumably with a very elderly daughter.
All of the problems we have mentioned and more besides would be solved at a stroke if we make a single assumption. It is this. Joseph was much older than 30 years old (41:46) when the two sets of seven years began (41:47). There are at least two possibilities here:
1. Joseph was actually older than 30 from Birth in 41:46. His years as a ‘son of 30 years’ [the literal Hebrew] could have been counted from his father giving him his coat. Or from his time in Egypt. We see a similar thing when Saul is supposedly one year old in 1Samuel 13:1. This verse gets some translators into a panic, but it is obviously not counting from Saul’s birth.
2. The seven years of abundance did not immediately follow Joseph’s appointment, even though the passage jumps straight onto this. There may have been a lengthy gap of (say) 10-20 years.
Although this solution is slightly problematic, I think my solutions are plausible and a simple problem is exchanged for a multitude of problems. My solution gives Judah time to have grandchildren and Benjamin as well, so Genesis 46 could actually be taken more literally after all.