[gil80]

Shield will upscale if you set it to do it. 
You can see the settings pressing the menu button and looking at AI upscaling. 

In Kodi libraries are not interchargeable between versions. 
But when you set everything up, just use Kodi Backup addon, back it up and restore. 

Just beware and pay attention to what version of the addon you're using. I wasn't able to restore a backup a had because of versions missmatch. 
I believe for Matrix it's version 1.64. So use that and when restoring use this same version.

Ok, I’ve done some DV testing.
MP4 files are playing well.
.ts DV files are broken. Getting spinning wheel of death. The .ts files were downloaded from LG’s website to demo DV on my OLED.
I don’t have .MKV DV files yet.

Also, this is not Kodi related but rather a bug in Shield, it doesn’t auto switch between Rec709 to Rec2020 if I play DV or HDR or SDR.
I had to set under Custom Display Mode to have the default value of Rec709 DV and HDR10 Ready for it to auto switch. If it is set to Rec2020 DV and HDR10 Ready, it won’t auto switch - just FYI for those who are interested.

Is your shield running the latest firmware?

It got automatic color space switching a few firmwares back.
You can enable and disable it.

.ts should not work since it uses dual layer dolby vision and this is not supported.

Yes, running the latest. The auto colour switching doesn't work, according to the TV HDMI service info menu when the Shield is set to Rec2020 DV and HDR10 Ready, regardless if auto-switching is enabled. It will only auto-switch between the profiles if Rec709 DV and HDR10 Ready is selected.
This is off-topic, of course, but interesting find. If you have an LG TV, I can explain how to test that.

p.s. - kodi 18.9 is using a lower version for the backup addon than kodi 19.0. I cannot restore due to some error which I have no idea about.