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I often delete emails by hitting the 'x' when the little popup window shows a new email, so they end up in my Deleted Items, but they still show as read (so DI is bold, and there's a number in parentheses after).

Where can I set it in Outlook so that all deleted emails automatically have 'read' status?

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Not exactly the answer you're looking for, but you can right click on the Deleted Items folder and choose "Mark All as Read." – Chris Oct 14 '11 at 19:07
Yep, I've actually been right-clicking and choosing to empty it instead, but that is the only option I've really seen. – Lance Roberts Oct 14 '11 at 19:11
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The commercial product, ReliefJet Essentials for Outlook (I am one of its developers), has a free feature: Outlook Tweaker. It provides a Mark deleted items as read automatically feature. Just check this box and all your messages will be marked as read when they are deleted.

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That worked great, thanks! – Lance Roberts Oct 25 '11 at 21:47
Unfortunately the full trial version of ReliefJet Essentials for Outlook has to be installed to get the "free" feature. This adds all the paid for functionality of the product including buttons on the toolbars. The "Mark deleted items as read automatically" feature does work, but the functionality reverts when the product is uninstalled, so as far as I know the only way to retain the "free" functionality is to purchase the product. – Leigh Riffel Nov 25 '11 at 14:12
Dear Leigh Riffel, you're so wrong :-( 1. This feature is not "free": it is free. 2. You can turn the toolbars off with a pair of mouse clicks. 3. There is no need to purchase the product if you don't need extra functionality. – thims Nov 25 '11 at 16:57
And one more thing to Leigh Riffel: if you uninstall any product, of course the functionality it provides is also uninstalled. – thims Nov 25 '11 at 17:06
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Trial software normally should be uninstalled or purchased when the trial is complete. Your implication is that the trial is indefinite, could you please suggest that this wording be added to the website? Please explain your "pair of mouse clicks" as it sounds much easier than what I have found: Right click Ribbon >> Customize Ribbon >> Uncheck ReliefJet Essentials >> OK, and Create New Email >> Right Click on Ribbon >> Customize the Ribbon >> Select ReliefJet Essentials >> Remove >> OK. – Leigh Riffel Nov 25 '11 at 18:38
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