ye esea didnt have STV+ or w/e so the damage number data etc. isnt recorded.

My Season 29 demos have hitsounds and damage numbers. Albeit, they only show up after the week 1 demos, but anything after that works.

I downloaded this demo in question and damage numbers/hitsounds work fine on my end.

These are the CE settings I use when looking at STVs.

ce_localplayer_enabled 1
ce_localplayer_player 1
ce_localplayer_track_spec_target 1
ce_antifreeze_enabled 1
ce_killstreaks_enabled 1
ce_hitevents_enabled 1
ce_hitevents_dmgnumbers_los 1

Also make sure tf_dingalingaling is set to 1 if you haven't done that already.

Make sure to get the CastingEssentialsRed builds, which are a lot newer.

Optionally use the following:

// Highlight player being spectated in killfeed
ce_localplayer_enabled 			1
ce_localplayer_player 			1
ce_localplayer_track_spec_target 	1

// Correct view heights for player POVs (sniper dot alignment etc.)
ce_cameratools_fix_view_heights 	1 // (might cause issues with the POV being stuck in the floor then set to 0)

// Fix weapon skins to always use highest quality texture
ce_weapon_skin_downsample 		0 // 0 = highest, 10 = lowest quality
ce_graphics_fxaa 			1 // optional fast antialiasing to reduce 'jaggies'

// Force killstreaks to be enabled and additive
ce_killstreaks_enabled			1
ce_killstreaks_hide_firstperson_effects 1

// Player Outlines
ce_graphics_improved_glows 		1 // 0 = TF2 glows, 1 = CE optimized glows
ce_graphics_fix_invisible_players 	1
ce_graphics_fix_viewmodel_particles 	1
ce_outlines_spy_visibility 		1

// Projectile Outlines
ce_projectileoutlines_mode 		1 // 0 = always, 1 = only when hidden, 2 = only when model visible
ce_projectileoutlines_pills 		1
ce_projectileoutlines_rockets 		1
ce_projectileoutlines_stickies 		1

// STV Damage Numbers & Critical Hit Particles
ce_hitevents_enabled 			1 // Enable events (requires srctv+ on server for damage numbers)
ce_hitevents_dmgnumbers_los 		1 // 0 = hide, 1 = show through walls
ce_hitevents_healing_crossbow_only 	1 // Only show Crossbow Healing numbers
hud_combattext 				1 // Damage numbers (text color below)
hud_combattext_red 			245
hud_combattext_green 			225
hud_combattext_blue 			205
hud_combattext_doesnt_block_overhead_text 1
tf_dingalingaling 			0 // Hitsounds (or use tf_dingaling_volume when 1)
tf_dingalingaling_lasthit 		0 // Killsounds (or use tf_dingaling_lasthit_volume when 1)

// Team names (defaults for possible filtering out racist team names in win panels or overriding for actual fixture)
// Max length 32 characters
ce_teamnames_blu 			"BLU"
ce_teamnames_red 			"RED"

Thanks for the help guys. I was able to get the first map of the S31 grand finals to work:

https://www.youtube.com/watch?v=wp9eVlk9iXQ

However TF2 kept crashing out when I enabled any of these cvars:
ce_hitevents_enabled
ce_projectileoutlines_pills
ce_projectileoutlines_rockets
ce_projectileoutlines_stickies
I made sure to use the CE r21-red06 build and I used almost the same settings as what Wiethoofd pasted - are there any known incompatibilities with other settings that I need to worry about? I disabled all other plugins but no luck.