Q1: If there are 7 cards in my hand and I have 2 of this Digimon at the start of my main phase, can I draw a total of 2 cards from both instances of this card's effect?
No, you can't. At the start of your main phase, the Start of Your Main Phase effect on 2 of this Digimon simultaneously trigger, then the player determines the activation order. However, because your hand increases to 8 cards from Draw 1 on the 1st Digimon, the effect's conditions aren't met for the 2nd Digimon, so the effect doesn't activate. As a result, you only draw 1 card.
Q2: If I have 7 cards in my hand upon an attack by my Digimon with 2 of this card in its digivolution cards, can I draw a total of 2 cards from both instances of this card's effect?
No, you can't. Upon the attack declaration, the inherited effects on the 2 copies of this card simultaneously trigger, then the player determines the activation order. However, because your hand increases to 8 cards from Draw 1 on the 1st card, the effect's conditions aren't met for the 2nd card, so the effect doesn't activate. As a result, you only draw 1 card.
Lv.3 Jellymon LM-002 U Rookie | Data | Mollusk [Start of Your Main Phase] If you have 7 or fewer cards in your hand, <Draw 1>. --- Inherited: [When Attacking] If you have 7 or fewer cards in your hand, <Draw 1>.
Lv.3 Jellymon LM-002 U Rookie | Data | Mollusk [Start of Your Main Phase] If you have 7 or fewer cards in your hand, <Draw 1>. --- Inherited: [When Attacking] If you have 7 or fewer cards in your hand, <Draw 1>.
Lv.3 Jellymon LM-002 U Rookie | Data | Mollusk [Start of Your Main Phase] If you have 7 or fewer cards in your hand, <Draw 1>. --- Inherited: [When Attacking] If you have 7 or fewer cards in your hand, <Draw 1>.
Lv.3 ジェリーモン LM-002 U 成長期 | データ種 | 軟体型 【自分のメインフェイズ開始時】自分の手札が7枚以下なら、≪1ドロー≫。 --- Inherited: 【アタック時】自分の手札が7枚以下なら、≪1ドロー≫。