A topic from AEG's L5R CCG Rules forum, copied for Oracle of the Void from a copy of the forum saved in October 2015, so pages it didn't save are missing. Players' names are left out; the rules officials are named. Rulings are as they stood on these dates; later rulings, the rulebooks and the Rules Archive may differ.
A player, 6 June 2015
House of Loose Silk
After a Personality is Recruited, you may bow and destroy this Holding to bow him, and you gain a Conspiracy token if his controller has no unbowed Personalities in play.
Could I use 3 of them on them same personality entering play to gain 3 tokens?
Jon Palmer (rules official), 7 June 2015
House of Loose Silk
Could I use 3 of them on them same personality entering play to gain 3 tokens?
Absolutely. The bow effect will fail to bow him once he is already bowed, but in each case, as long as the "no unbowed Personalities in play" clause is met, you will gain a Conspiracy token.