The title “Reborn Rich” was not about Yoon Hyun Woo being re-born as Jin Do Joon. It was about Jin Do Joon being reborn as Yoon Hyun Woo and becoming rich!

1. Yoon Hyun Woo did not die, he was in a coma for 1 week. He can not be reborn at all.

2. When Jin Do Joon died in the 2nd car crash, Jin Do Joon was reborn as Yoon Hyun Woo. Who later became rich.

3. The “Timeline 2” did not exist. As Yoon Hyun Woo said so himself that it was not time travel, nor possession. It was a repentance for both Jin Do Joon and Yoon Hyun Woo.

Everything else happened, other than the small changes (he was just recalling a previous life he should not be able to recall at all, that's why there were small changes), exactly the way it did.

“Reborn Rich” also meant being a new person, rich with values.

“Reborn Rich” also meant being reborn as a new person after his brush with death, and coming out of the coma (was “reborn”).

Re: Repentance
1. As Yoon Hyun Woo, this is his repentance because he chose money over reporting the murder.

2. As Jin Do Joon, it is his repentance because he did do things he shouldn't, he actually became his grandfather in the end.

When Jin Do Joon was reborn as Yoon Hyun Woo, it was his chance to repent as Jin Do Joon (previous life) and as Yoon Hyun Woo (present life).

In the end, Yoon Hyun Woo became part of Miracle, the company he founded in his previous life as Jin Do Joon.

That was one heck of a story twist. Totally unexpected.