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Before I begin, let me just say that I had a large gap in my DP usage from when I used version 3 back in college and using version 10 now. So if this is a simple solution, this may be why I'm missing it.

I'm trying to use my bluetooth headphones to listen to my DP MIDI mix, but when I pair my headphones with my computer, the mix still plays over the built-in speakers. I tried to find where I could switch the output to my headphones, but the only thing I could find in the manuals was to switch it in the "Configure Hardware Driver" window. When I do this, the mix starts playing in my headphones, but then several notes in my sequence get dropped during playback. And then even when I go back to the CHD window and switch it back to the original settings, those same notes still get dropped. The only way I can restore the expected playback (albeit still over internal speakers) is to quit DP without saving and restart it.

Expected behavior: To hear my MIDI mix as expected in bluetooth headphones
Actual behavior: Hearing notes missing during playback
OS: Mac OS 10.14
DP Version: 10.11

You need to switch the output in the Mac sound preferences. You might need to change the output in your DP bundle output to your Bluetooth headphone/device as well. This could involve creating a new bundle.

You've not given enough info on your setup for a definitive answer. What is driving your BT headphones? System audio or your recording interface. I'll give it a stab anyway.

If using System audio for playback, your Sound Preferences need to show an input when your BT driver is active. Once that is set, you can switch back between your interface and System audio in Configure Hardware Driver without going back to System Preferences. I do this multiple times a day—my phones are driven by my interface while my studio monitors are driven by an interface connected to the headphone out.

In DP 10.11 over Mojave, you should only have to change your bundle in DP Setup/Configure Audio System/Configure Hardware Driver. Select whatever is driving your BT headphones if they are on and don't show up in the list.

Mojave needs to be 10.14.4 or later to ensure compatibility with all recording interfaces. Let's just say there were major issues between some devices and Mojave 14.0–.3 and minor issues with many others.

Yes, more info on the setup would probably help. Is a USB MIDI device involved? On my setup, older bluetooth devices (original trackpad and Apple mouse from 10 years ago) have intermittent connections when there is a nearby MIDI device connected via a USB 3 port, or there is a WIFI signal that is not 5G. I got around this by positioning devices getting a new trackpad and going to an older non BT mouse.

Okay, a little more info - yes, I have a MIDI iRig Keys IO, which has a built-in audio interface (that I am not currently using). The other piece of info that I don't know if I just forgot to mention or maybe I thought it was implied is that I can hear other audio applications (like YouTube) over my headphones, so it's something unique to DP that's causing the issue.

Does that answer your questions, or do you need more info?

You do not seem to understand how this is supposed to work.

I can hear other audio applications (like YouTube) over my headphones,

Take a look at System Preferences/Sound. You appear to have that set up correctly.

so it's something unique to DP that's causing the issue.

No reason to think that at all. Reread the previous posts. Follow my instructions to to open Configure Hardware Driver and select your output device.

After saving, your tracks should migrate to that same input/output bundle automatically. If not, you will need to select it manually in each track this time.

As long as you check your settings in Configure Hardware Driver at the start of every project, your tracks should follow automatically.

This is covered in the DP Manual and Quick Start Guide and training videos. This is part of the basics for DP and hasn't changed (except for the automatic part when you change devices).