you should be fine as long as you don't send btc from wallet #2 to wallet #1 too frequently. though if you want to be sure that you won't tracked, you can always use an exchange or a dice site to completely hide your track.
and multiple wallets "privacy" is not very different than multiple address.
Does a dice site deposit... Then withdraw, act as a true mixer? I would think the taint would be rather high... Perhaps even some of the withdraw coming back from the original deposit address
Just curious.
Strato