

Q1: If I use this card's On Deletion effect to DNA digivolve into Millenniummon in the hand, do the DNA digivolution requirements have to be met for Millenniummon?
Yes, the DNA digivolution requirements have to be met. In addition, DNA digivolution can't be performed unless the Millenniummon has DNA digivolution.
Q2: Does this card's On Deletion effect allow my Machinedramon and this card itself in the trash that activated the effect to DNA digivolve into Millenniummon in the hand?
Yes, that's correct. The On Deletion effect activates after the card is placed in the trash, therefore this card itself in the trash can DNA digivolve into Millenniummon in the hand.
Q3: What are the areas where Machinedramon and Kimeramon can DNA digivolve into Millenniummon in the hand using this card's On Deletion effect?
Your Machinedramon in the battle area and Kimeramon in your trash can DNA digivolve into Millenniummon in the hand.
Lv.5 Kimeramon BT18-015 R Ultimate | Data | Composite [When Digivolving] [When Attacking] By deleting 1 of your Digimon, delete 1 of your opponent's Digimon with the lowest DP. [On Deletion] 1 of your [Machinedramon] and 1 [Kimeramon] in the trash may DNA digivolve into [Millenniummon] in the hand. --- <Security A. +1> (This Digimon checks 1 additional security card.)
Lv.5 Kimeramon BT18-015 R Ultimate | Data | Composite [Digivolve] Lv.4 w/[Composite] trait: Cost 3 [When Digivolving] [When Attacking] By deleting 1 of your Digimon, delete 1 of your opponent's Digimon with the lowest DP. [On Deletion] 1 of your [Machinedramon] and 1 [Kimeramon] in the trash may DNA digivolve into [Millenniummon] in the hand. --- <Security A. +1> (This Digimon checks 1 additional security card.)
Lv.5 Kimeramon BT18-015 R ultimate | Data | Composite [Digivolve] Lv.4 w/[Composite] trait: Cost 3 [When Digivolving] [When Attacking] By deleting 1 of your Digimon, delete 1 of your opponent's Digimon with the lowest DP. [On Deletion] You may DNA digivolve 1 of your [Machinedramon] in play and 1 [Kimeramon] in the trash into [Millenniummon] in the hand. <Security A. +1>
Lv.5 キメラモン BT18-015 R 完全体 | データ種 | 合成型 【進化時】【アタック時】自分のデジモン1体を消滅させることで、最もDPの低い相手のデジモン1体を消滅させる。 【消滅時】自分の「ムゲンドラモン」1体とトラッシュの「キメラモン」1枚で手札の「ミレニアモン」にジョグレス進化できる。 --- ≪Sアタック+1≫(このデジモンがチェックする枚数+1)