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Bug Confirmed:

This is for the quest Get Junior on patch 1.07.

These two states will fail no matter which way you do the quest. If you refuse the invitation after playing cards, you will fail "Play cards with casino guests." But you won't fail "Search the casino for more information about Whoreson."

Inversely, if you take the invitation you will be immediately taken upstairs, that room is actually the one you're looking for when it says to "Search the casino for more information about Whoreson." This causes that objective to fail but it marks "Play cards with casino guests," as complete.

I've done it over 5 times now and I can't get them both to go green check mark on either outcome.

You will fail one or the other.

Note: I went to the casino first and I am currently thinking about Cleaver's offer for TGoN.