I've found that "wireless" headphones tend to have base units with different audio-input connectors while BT headphones only support a BT connection to the audio source. So with wireless units you can use a cheap HDMI audio splitter for RCA/Phono or 3.5mm Jack input to the headphones, and there's no dependency on having multi-audio output on the source, which is rarely supported. In LE you might be able to make multiple audio outputts work via Pulse audio (not the default alsa arrangement) but it's not a standard configuration so there's no HOWTO guide we can point you to.
Amazon searching "wireless headphones for tv watching" threw up some options for me. These were the simplest/cheapest ones (no idea what they are like, but you can see they have lots of connectivity options). If the TV itself supports multi-audio out you can connect them direct. If not you might need some kind of HDMI splitter to get an RCA output or similar.
NB: Pulse audio almost certainly can output to multiple devices at the same time with the right config (which you'd have to Google). The tertiary challenge with multiple outputs is often "audio sync" as processing times for the BT audio path vs. the HDMI path may end up being a little different.
... searching "wireless headphones for tv watching" threw up some options for me. These were the simplest/cheapest ones (no idea what they are like, but you can see they have lots of connectivity options). ...
pacmd complains that there is PulseAudio no daemon running and as soon i reboot LibreELEC all changes i did with pactl were gone. no idea where to put all the profile, config and script files to LibreELEC to keep the config persistent and/or get executed automatically.
without rebooting i never saw any new audio devices (sinks) in Kodi i could select.
I spent some time to get working the dual audio output (DAC & HDMI) with PulseAudio on my RPi3, was unstable and the quality wasn't the best. Because I don't need really simultaneous audio (DAC for net radio & hdmi for TV and movies), I'm using now the "Audio Profiles" add-on and is the perfect solution for me.
If you need real simultaneous audio, use the solution proposed by chewitt, if your TV have any usable audio output, use it as audio source for headphone, if not use hdmi-audio splitter.
Our current setup is to connect the source devices to the TV via HDMI, then run a digital audio cable from the TV to the digital audio input of a Sony HW700DS headphone transmitter. This transmitter has a digital audio loopthrough capability so I route the audio out from it to a soundbar.
The headphone transmitter actually has three HDMI inputs and one output so it is intended to be used as a source selector but a) you have to actually walk up to it and press one of three buttons, b) it's HDMI 1.4a so no HDR and c) I'd need something to split out the audio for the headphones.
Never tried with Bluetooth speaker. Once had a working config with simultaneous sound on TV and Speakers (from audio jack), was a delay between outputs and created a strange (annoying) echo... maybe can be resolved that too, but I never had a stable and good sound quality config for simultaneous audio.
The longer idea was to create a suround sound system with bluetooth speaker for TV, and use stereo for music and distribute the speakers in several rooms (kitchen, garden, bath). But now I would be glad If I only get the speakers simultanous autput.
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