would you split chips multiple times to aid privacy?
If you had multiple people to send funds to then this makes sense (and withdrawing 4 equal sized smaller chips compared with 1 big chip is obviously going to do better to hide the trace between the funds you deposited and withdrew - especially if you withdraw at different times).
If you're paying for multiple things or multiple people, it might also be useful for hiding the link between you and them (especially if you're paying them different amounts for a similar service or something).
And would you leave chips for a while before withdrawing?
The general recommendation I've seen from research on this is 2-7 days normally delivers maximum privacy at hiding the link between your deposits and withdrawals.