So it seems a bunch of LI path checks were busted in 15.0.2. Quickly re-ran through the update in 15.0.3 using skip function, and this time got the Amber and Penelope list scenes without any KCT checks.
The Penelope and Jenny drinking scene now actually acknowledges your sleepover with Penelope; while in 15.0.2, the two just randomly teased you about chasing after others, which seemed pointless and awkward.
Also, unlike 15.0.2, Aubrey doesn't brush you off at the wedding if you express interest in getting serious in the future.
The 0.3 path bug fixes certainly alleviated many concerns I had from the 0.2 update.