Q1: If this card's "Overclocking《Feature「Puppet type》》attacks a "messenger" token by deleting it, are this card's When Attacking effect and the "messenger" token's On Deletion effect triggered at the same time?
Yes, simultaneous triggers.
Lv.6 Cendrillmon EX7-030 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.) [Start of Your Main Phase] [When Digivolving] You may play 1 [Familiar] Token. (Digimon/Yellow/3000 DP/"[On Deletion] 1 of your opponent's Digimon gets -3000 DP for the turn.") [When Attacking] 1 of your opponent's Digimon gets -6000 DP for the turn.
Lv.6 Cendrillmon EX7-030 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.) [Start of Your Main Phase] [When Digivolving] You may play 1 [Familiar] Token. (Digimon/Yellow/3000 DP/"[On Deletion] 1 of your opponent's Digimon gets -3000 DP for the turn.") [When Attacking] 1 of your opponent's Digimon gets -6000 DP for the turn.
Lv.6 Cendrillmon EX7-030 SR Mega | Virus | Puppet/LIBERATOR <Overclock ([Puppet] trait)> [Start of Your Main Phase] [When Digivolving] You may play 1 [Familiar] Token (Digimon/Yellow/3000 DP/[On Deletion] 1 of your opponent's Digimon gets -3000 DP for the turn). [When Attacking] 1 of your opponent's Digimon gets -6000 DP for the turn.
Lv.6 サンドリモン EX7-030 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) 【自分のメインフェイズ開始時】【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1体を登場できる。 【アタック時】ターン終了まで、相手のデジモン1体をDP-6000。