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It is high on my list because I think most miners (and pools) would be happy to include many more free transactions than the current rules allow, and if there is another price spike or somebody rich decides it would be fun to make the block chain a couple of gigabytes bigger it is much easier to react if the fees are not hard-coded.
The rough plan is:
+ Give miners more "knobs" to set fee policy-- let them specify (via command-line switch and maybe bitcoind RPC command) how much (if any) space to set aside in blocks for free transactions, how much to charge per-kilobyte and/or per-ECDSA-signature-validation, and what the priority/size/number-of-signatures thresholds are for considering a transaction for inclusion in the free space.
+ As Meni says, teach clients to look at the recent blockchain history and, for a given transaction, estimate how much of a fee will be required to get it into a block reasonably quickly. Maybe a "createtransaction" RPC call that locks coins for a certain amount of time and returns the how-long-to-confirm estimate along with "commit/aborttransaction" calls....
+ Figure out a reasonable UI for fees. Maybe: calculate the probability sending the transaction with 0 fee will get into the next, oh, 3 blocks, and if it is greater than, oh, 90% then just send it without a fee. Otherwise, let the user decide between paying a fee that will get it included (with 90% probability) in the next 3 blocks or letting them know how long it might take if they pay no fee.
Lots of details to be worked out...