Q1: Familiar Tokens have an On Deletion effect, but because tokens are removed from the game instead of being placed in the trash when deleted, does this mean that the On Deletion effect doesn't activate?

Tokens aren't placed in the trash when deleted, but On Deletion effects on tokens will activate as if the token was a Digimon.

Data Sources

Official English Card Listworld.digimoncard.com

Lv.6 Cendrillmon      ST19-12  SR
Mega | Virus | Puppet/LIBERATOR

<Overclock ([Puppet] Trait)> (At the end of your turn, by deleting 1 of your Tokens or other [Puppet] trait Digimon, this Digimon may attack a player without suspending.)
<Blocker> (This Digimon can block in the blocker timing.)
[When Digivolving] You may play 2 [Familiar] Tokens. (Digimon/Yellow/3000 DP/"[On Deletion] 1 of your opponent's Digimon gets -3000 DP for the turn.")

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Inherited: ー

Official English (Asia) Card Listen.digimoncard.com

Lv.6 Cendrillmon      ST19-12  SR
Mega | Virus | Puppet/LIBERATOR

<Overclock ([Puppet] Trait)> (At the end of your turn, by deleting 1 of your Tokens or other [Puppet] trait Digimon, this Digimon may attack a player without suspending.)
<Blocker> (This Digimon can block in the blocker timing.)
[When Digivolving] You may play 2 [Familiar] Tokens. (Digimon/Yellow/3000 DP/"[On Deletion] 1 of your opponent's Digimon gets -3000 DP for the turn.")

DCG Wikidigimoncardgame.fandom.com

Lv.6 Cendrillmon      ST19-12  SR
Mega | Virus | Puppet/LIBERATOR

<Overclock ([Puppet] trait)>
<Blocker>
[When Digivolving] You may play 2 [Familiar] Token (Digimon/Yellow/3000 DP/[On Deletion] 1 of your opponent's Digimon gets -3000 DP for the turn).

Official Japanese Card Listdigimoncard.com

Lv.6 サンドリモン      ST19-12  SR
究極体 | ウィルス種 | パペット型/リベレイター

≪オーバークロック《特徴「パペット型」》≫（自分のターン終了時、自分のトークンか特徴に「パペット型」を持つ他の自分のデジモン1体を消滅させることで、このデジモンでレストせずにプレイヤーにアタックする）
≪ブロッカー≫（このデジモンはブロックタイミングでブロックできる）
【進化時】「使い魔」（デジモン• 黄• DP3000• 【消滅時】ターン終了まで、相手のデジモン1体をDP-3000。）トークン2体を登場できる。

Rulings

Data Sources

Japanese Rulings