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For investigators that start with a Blessing or a retainer, do they need to roll to check if they discard the blessing or retainer during their first upkeep?

Also, do investigators that gain one of these cards during the game only after roll to check if they discard after holding that card for one turn or do they check on their first upkeep as well?

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From the Arkham Horror rulebook (page 6: Upkeep: Perform Upkeep Actions)

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

Regardless of when and how you acquire the card (including during setup), you always have one Upkeep for which you do not roll to lose the card.

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