How much $ in used gear streaming to beat $5000 CD player

Paulcreed Soix suggestion will astound you , imagine a huge music library with a touch of a finger on your iPad , phone ect including worldwide internet FM, no computer skills required. 

Innuos servers / streamers are one of the very best sound quality on the market today including AudioMirrors SE dac this would certainly be a fabulous choice .

Paul - the benefits of bypassing the Computer and going straight to the purchase of the streamer (Innuos) in combo is where a lot of magic happens. Far more musical!

I don’t have the Tubadour but given the reviews it’s a solid bet. You can obviously start stock and upgrade to SE later for a significant improvement if that works better for budget reasons. I personally hate dealing with computers and will never use one as a source so a streamer would be mandatory for me, but good sound is certainly possible through a computer if you have the knowledge and/or patience. A used Zen Mk3 and a new Toubadour SE would be about $5k, so if that’s your budget I’d just bite the bullet and solve everything at once. You’ll be thrilled, and life’s too short.

$2000-3000

pick a decent streamer, then pair with chord qutest or rme adi 2 - if you like sweeter softer sound lil tubey try lampizator or higher schitt multibit like yggrasil