I've got answers. Apparently very long ones.
1) So, the date is a story event and not part of the replays (mostly because it's not an intimate scene). Here are the exact requirements for the date with Lani at the guild:
- Had the conversation in the initial massage scenes and agreed to have the date (available at the first massage scene after the second spar, not available if already slept with Lani).
- Lani is in your party.
- Lani's level is more than 1 (so she's fought with you at least once).
The only block is that it skips this initial relationship scene if you're already intimate and moves you directly into later scenes.
On the other hand, the second event in the hint page is the continuation of the massage scenes, which is really poorly worded in this version of the game. I changed the wording a little in the recent premium release, but I still try to be a little vague... anyway, here are the requirements for that scene:
- The first massage is forced after your second sparring victory, but no additional scenes are triggered until other requirements are met.
- Additional massage scenes are triggered at a 15% chance in the evenings if Lani is in your party, and Lani has moved far enough in camping content (scene 5 of the normal tent or scene 2 of the dungeon tent).
- Once the additional massage scenes trigger, they follow a standard progression. 2 shoulder scenes, then the final scene is available after Lani's affection reaches 250.
- The game jumps directly to the final scene if you've slept with Lani.
Upon some inspection, that jump may be making it quite difficult to get... the game uses label markers to know if you've seen a specific scene for the purposes of replays, and it looks like that label is skipped if you access the last massage scene outside of the standard progression.
To unlock the scene directly, you can use a console command (assuming you're on PC). Just open the console (shift + O) and type in:
renpy.mark_label_seen('lani_massage_choice')
I'll make a correction to allow the other methods to also unlock the scene, but that will need to be in later versions.
2) Challenger lowers the damage restrictions that are added when fighting enemies that are higher level than the player. There are some pretty heavy debuffs on damage dealt in the beginning, and the maximum title level removes all of those calculations, and adds on a 50% buff when fighting enemies higher than your level. (The damage reductions are exponential, hence the strange wording in the title descriptions.)
In order to improve the title (and lower the restrictions), you need to defeat an enemy higher than your average party level (so if Lani is 1 and Liam is 19, the average party level is 10). The higher over your level the enemy is, the higher the title will develop, with the maximum title level earned after defeating an enemy 45 levels over your own.
Note, you only need to defeat one enemy of that level difference. The game doesn't currently make any use of the number of enemies of various levels you've killed.