"port a checkbook into a ledger" and "smile sb's approval"??

Factual Questions
1

Hi

Please explain the following phrases. The first one makes no sense to me. The second one I believe I understand, but I just need to get a second opinion. I look forward to your feedback.
davidmich

1.“port a checkbook into sb’s ledger” p. 68 “Steve Jobs” by Walter Isaacson
referring to Elizabeth Holmes…part-time bookkeeper for Apple

“figure out how to port Jobs’s checkbook into a ledger”
2.“smile sb’s approval”??p. 148 on Karl Marx and Jenny von Westphalen marriage
“But she was in love with him, and both families smiled their approval”

Was this a happy approval or just one of resignation?

2

“porting” in computing is converting a program written for one system so it can run on a different system. It reads to me like a quirky computer person way of saying Job’s personal accounting wasn’t up to bookkeeper standards, so it was a bit of an art making it fit the company books.

3

As per Merriam-Websters:

4

Who is “sb”?

5

Abbreviation for somebody?

6

yes sb stands for somebody.

7

Thank you all. Very helpful.
davidmich