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Page 6 of the reference guide says:

Bless, Curse, Bank Loan, and Retainer cards do not require an upkeep roll during the first Upkeep Phase after an investigator acquires them.

Does this mean we skip the Upkeep instructions entirely or merely skip the roll portion? Essentially, upon obtaining the card, do we benefit from gaining $2 without needing to roll to see if we discard the card?

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It means you merely skip the roll (you do not skip all upkeep instructions)

"It's like a salary. You usually get them through encounters. Darrell Simmons and Rita Young also start with one."

https://boardgamegeek.com/thread/397466/retainers

"If you have a copy of a "special" card, i.e. Retainer, Blessing, or Curse, and you receive another one, it replaces the first copy. This effectively means you will not roll during the next Upkeep to see if you lose the new copy (the old copy has already been replaced and lost)."

https://community.fantasyflightgames.com/topic/50931-two-retainers/

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    Also that's what it says in the rules quoted in the question - skip the roll, not ignore the card.
    – Cascabel
    Commented Jun 11, 2016 at 16:20

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