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[TheDreadPirate]

My questions at this point are:

• Will the setup listed above have any issue with 10bit HDR bluray rips in either MKV or MP4 formats?
  

That setup is fine in terms of performance, but AMD lags a bit in terms of quality.

• Would a chromecast (Either version) work instead of the shield?
  

All the "dumb" Chromecasts are EOL and Jellyfin's casting functionality is a bit jank anyway.  Stick with the Android TV Chromecast or some other Android TV device.  I have two of the CCwGTV 4K models and am pretty happy with them.

• Would I even need a client if I just used the web interface on the TV or went through the pain of sideloading it? (I tried to do this on my current samsung TV and nearly ripped my hair out, but I'll try it again if it's viable lol)
  

I'd choose an Android TV/Roku dongle/box over using anything directly in the TV every day of the week.  It will be a much better experience.

• More out of curiosity, would I run into any issues if I decided to re-encode my library into AV1 on either the hardware or software side?
  

There are a few quirks in 10.8 that cause AV1 to be converted to HEVC or H264 unnecessarily.  But 10.9 is around the corner and that issue is resolved.  A surprising number of mobile devices support AV1, but a surprising number of TV dongles/boxes don't support it yet.  Unfortunately the current CCwGTV 4K doesn't, but the HD model does but no HDR.  But an updated CCwGTV 4K is rumored to be out soon and will support AV1 AND HDR.

I have been encoding my library with AV1 to A) save space and B) save bandwidth (only 40Mbps up).