Halloween: The Game Chapter 5: all 6 challenges
Chapter 5 swaps residents for police officers, which changes the pace: they carry flashlights and they look for you. Several of its challenges are about handling that rather than about executions.
One challenge here is genuinely unreliable. The walkthrough this was compiled against reports failing the Loomis-related challenge repeatedly despite never being detected, which suggests its condition is stricter or buggier than its description. If you fail it without being seen, you are probably not doing anything wrong.
Challenge 1Two flashlights at once
Goal: Disable two officers' flashlights with a single use of the ability.
You need two officers standing together. A reliable pair appears on the north side, just before the sewer entrance on the right. Use the ability once while both are in range.
Challenge 2Pitchfork execution
Goal: Execute a police officer with the pitchfork.
Leave the spawn area, turn right, and continue a short way. The pitchfork leans against a house wall just left of a parked car.
Improvised weapons
Challenge 3Three residents
Goal: Take down three residents before escaping.
Head right from the restroom and check the houses along that side. Three is easily reached without crossing the map.
Challenge 4Officer in Wallace's house
Goal: Deal with a police officer inside the Wallace House at Tier 3.
Build to Tier 3 first. If no officer is inside when you arrive, make yourself briefly conspicuous near the officers outside to draw one in.
Stalk tiers
Challenge 5Escape undetected by Loomis
Goal: Get out without Loomis detecting you.
Known to be flaky: it has been reported failing on runs where Loomis never detected the player at all. Escape via Shape Jump and, if it fails without an obvious cause, retry rather than changing your route.
Challenge 6Chapter clear
Goal: Finish Chapter 5 with the remaining objectives complete.
Fold this into the run where you are not attempting the Loomis stealth challenge, since that one is the most likely to force a restart.
Story mode difficulty runs Normal, Hard, Boogeyman. Nothing published indicates a challenge is gated behind a difficulty setting.
Keep going
Sources: Official site