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This sounds like you may need to create something like an HTML web resource to render the accounts and use Jscript to perform the remaining actions based on the records selected by the users. Otherwise, have you tried just a view of the relevant accounts and then selecting them all to reassign at once? Perhaps you could then have a workflow fire when the account owner changes that updates the two fields on the account record with the appropriate values. Not as user friendly as a dialog but may work if you don't want to do any customization.
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