Regarding Reliable Talent, one interesting quirk in the rules is that it has absolutely no effect on passive scores.
If you want to really challenge a high level rogue with expertise, throw in an encounter that requires extended/repeated activities with with lots of opportunities to apply advantage or disadvantage on the opposing checks (roll for trap and hazard DC's instead of using static values). As the DM, roll in the open when possible as the rogue faces any obstacles. Avoid hard, binary fail states and be sure to include interesting choices and decision points in both success and failure so the player doesn't feel like the scene is on autopilot. And don't overuse this technique because players enjoy rolling dice.
If you want to really challenge a high level rogue with expertise, throw in an encounter that requires extended/repeated activities with with lots of opportunities to apply advantage or disadvantage on the opposing checks (roll for trap and hazard DC's instead of using static values). As the DM, roll in the open when possible as the rogue faces any obstacles. Avoid hard, binary fail states and be sure to include interesting choices and decision points in both success and failure so the player doesn't feel like the scene is on autopilot. And don't overuse this technique because players enjoy rolling dice.
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