I have a Google chromecast with google tv on one of my other televisions. Probably going to move over to that. I have tv optical out going into an avantree transmitter with a passthrough going to a soundbar underneath. The transmitter transmits to both a small soundbar on other side of the room and a set of headphones. Works perfect. The small soundbar helps with voice clarity when i dont want the tv too loud. and headphones are there for when needed.
Roku Streambar also does NOT support earbuds that I need due to a hearing loss. I have to move to another stream device because Roku is years behind.
Roku Voice Remote Pro has a headphone Jack or you can plug a computer into your HDMI port and use the computers Bluetooth for your earbuds as long as you're watching most everything on your computer instead of streaming apps I recommend a long range Bluetooth adapter for your PC if you go that route