If I was starting from scratch with your budget I'd by a Bluesound Node ICON and a Qobuz or Tidal subscription.
If you have SXM radio in your car, the BluOS has native integration which is free and is great for casual/background listening.
Wait a year and when the warranty runs out add a Teddy Pardo linear power supply.
IMHO this will get you a long way, with a neat and tidy one-box solution with a good app.
You'll need to spend 3-5x for the next upgrade.
I just demoed the ICON in my system. See my mini-review here if your are interested.
I strongly recommend ethernet rather than WiFi with the ICON.
Good luck.

