The software ecosystem is missing a useful piece:
When you are receiving regular payouts, from a job salary or mining pool for example, there needs to be address rotation.
Right now, the only way to do that is manually logging into the payer's website, and replacing the current payout address with a new one.
Software should communicate with the payer, or give the payer a list of addresses, or an HD seed that may generate additional public keys, etc.
Address reuse in these circumstances is annoying, hurting privacy, but inevitable until software improves.
This is (basically) my argument at the moment against this. In the case of BTC Guild, the *highest* level of security an account can have is locking the wallet address. With this, you can not change it unless you digitally sign a message using the private key, confirming ownership. Removing the lock is a manual process, nothing on the site is capable of removing the wallet lock once it's in place (even an SQL injection would not be able to do it due to lack of permissions).
Similarly, it discourages automatic payouts, since those would use the same address every time unless changed. The last thing I want is automatic payouts adding hassle, considering they're the best way to encourage users to not use the pool as a bank.
The only fix on this I can see would be on my end adding some kind of "wallet queue" to accounts where they can pre-make a batch of wallets to use (maybe even using the BIP32 suggestions), but my limited knowledge of BIP32 leads me to believe this would still require manual entry on the user part. If somebody else could generate the chain of public addresses to use, it seems like it wouldn't be very anonymous (they'd actually be able to follow all your transactions forever on that wallet-chain?).