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To be honest I think overall opinion on how these prefs will work is divided enough that I think all options should be implemented. Doing one or the other is going to leave a significant portion of users unhappy. Here's my all-inclusive suggestion:

  Opening files in Cog: [X] Plays the file
                        [ ] Enqueues the file
              (Hold shift to reverse this preference)

Clear playlist on Open: [X] Enabled
                        [ ] Disabled
           (Hold CMD+Control to reverse this preference)

I agree that it might be too many preferences and/or too many modifier keys, but in the end I think it's something everyone can agree on? This could further be refined by utilizing a hotkeys preference pane (to remove the "Hold such and such key to reverse this preference" text) to allow user defined keys for reversing both of these settings (if the user even wants such a thing).

My personal opinion of the setting is either this, or how I had it in the mockup. I'm always open to other ideas, but ideally I don't want to open an mp3, have it play automatically and have it _always_ wipe my playlist. On the flip side I don't want to always enqueue a file just to keep my playlist from being wiped.

Edit #2: This forum really need a preview button.

The separator line issues are a mistake on my park - when I resized the window it cut 'em off. And I did forget a separator - as you can kinda see by the spacing.

I also don't know how to do a mockup with a toolbar on top - Interface Builder only shows me that screen, and had all the tabs in separate windows. I would say the above page would be called "General", then we'd have a "Hot Keys" tab, and then tabs for whatever plugins decide to add a tab.

Whoops! I meant 'shift'.

I understand the simplification point of view, but while many options might seem scary - a lack of them or oversimplification may actually be detrimental. Sure everything is separate and categorized, but now you're in the position of creating a new category for nearly every preference - and in the end may need to simply create a "Miscellaneous" tab for options that don't fit anywhere else. While it seems Cog is trying to move away from it in many ways, I think iTunes could be a somewhat decent example of a preference pane. If an application designed to be "the" music playing app/store for both Windows and Mac can have a large number of options, many of them on the same page, why can't Cog (an application that many users switch to simply to get away from iTunes simplicity and lack of options) consolidate options?

Eventually Cog is going to support a plugin architecture, and eventually it may support things like tagging, replaygain, applescript support and so on. What I'm trying to get across is, what kind of application are you guys writing? Is your target audience the same as iTunes? Are options going to be removed/simplified for the "general masses" so that even my grandmother could use it? Is it going in the direction of foobar2000, which is so extensible that every tiny little bit of the application can be replaced and modified? Something inbetween, in my opinion, is the best route - but I think a middle ground should be settled and justified before simplifying on end of the application while adding "complicated" features on the other end.

To further my case, I'm going to try and get together a mockup of a consolidated preferences page. On that note, I really think this should become a separate thread now. Sorry for going off topic guys!