A question about headphones

Since you want to ’test’ the waters, and given your opening post: go over ear, closed back, Bluetooth 5.3 (5.2 at least). BTW, the Bluetooth version needs to be supported both on your phone (for instance) and your headphone (to get the full benefit of the version).

If the pair you go with works to your satisfaction with BT, it will perform better wired. However, your need for a 20 foot long cable is fairly long and that length will require careful selection and audition (i.e. might pose pairing issues with a headphone amp and the type of headphone you choose) .

With BT you can skip the headphone amp and cabling (for now) while you are figuring out how to move forward.

Check out sites like Headfonia, Headphone.guru, Headphonics, etc. for recommendations and reviews.

B&W just released the PX8 (slightly above your current budget). The previous PX7 S2 is available well within your budget.

@r042wal It seems you are ’new’ to headphones / headphone systems. I encourage you to keep the first steps simple.

Figure out which headphone(s) you like / enjoy / appreciate. The easiest way to do this is to start with a mainstream option. The advantage is the price point, ease of trial and return, up to date in terms of wireless specs/codecs, and a quick re-sale via a local site like craigslist. You can usually listen / audition at your local best buy or equivalent store.  Most of these options will come with ANC, but it can be turned off. ANC does come handy and you may wish you had the option when you realize so. They are also fully portable and will not restrict you to your audio room.

If you go wired, it moves from a bit more complicated to much more complicated. You are already trying to make the step of using aspects of your current system...which can be fraught with issues and a domino effect (typically not in a good way and in dollars spent) for someone just starting out.

There are mainstream options within your budget that are both wired and wireless.

The first sentence of your opening post points to "needing your wife to enjoy her sleep." Open back headphones are typically superior sonically but they do bleed sound.

There are tradeoffs all around. And it is not straightforward.

I’ll reiterate: since you are new to this start basic. Learn. Move on with a greater understanding and to better and wider options.

All of the major players in the mainstream wireless space have decent offerings within your budget, and with budget to spare.

If you want to dig deeper, go over to headfi.org

@r042wal   Keep us posted on your journey.

Just came across this YouTube panel 'review' of Wireless / ANC headphones across price points. They do a good job covering general points and you may find the perspective on wireless vs wired, at the end of the video, informational.

ecoustics: Best Wireless Noise Cancelling Headphones 2022

@r042wal   Congratulations. Great to hear you "couldn't be happier.' 

I purchased a 'new to me' Shitt LYR 2 headphone amp and a pair of Hifiman HE-R9 cans.  To sum it up, I couldn't be happier for a first time setup