Gideon's Company

• WWizards of the Coast2019-05-03
  Official Ruling
  Putting a loyalty counter on a Gideon planeswalker doesn’t cause any of its activated abilities to become activated.
• WWizards of the Coast2019-05-03
  Official Ruling
  The ability of Gideon’s Company triggers just once for each life-gaining event, whether it’s 1 life from Ajani’s Welcome or 2 life from Battlefield Promotion.
• WWizards of the Coast2019-05-03
  Official Ruling
  If you gain an amount of life “for each” of something, that life is gained as one event and the ability of Gideon’s Company triggers only once.
• WWizards of the Coast2019-05-03
  Official Ruling
  If Gideon’s Company is dealt lethal damage at the same time that you gain life, it won’t receive counters from its ability in time to save it.
• WWizards of the Coast2019-05-03
  Official Ruling
  Each creature with lifelink dealing combat damage causes a separate life-gaining event. For example, if two creatures you control with lifelink deal combat damage at the same time, Gideon’s Company’s ability will trigger twice. However, if a single creature you control with lifelink deals combat damage to multiple creatures, players, and/or planeswalkers at the same time (perhaps because it has trample or was blocked by more than one creature), the ability will trigger only once.
• WWizards of the Coast2019-05-03
  Official Ruling
  In a Two-Headed Giant game, life gained by your teammate won’t cause the ability to trigger, even though it caused your team’s life total to increase.

Rulings via Scryfall