Here is an update to confirm that as long as you got a Thunderbolt device in the chain before the DisplayPort monitor, it should work just like the "old days", my setup:
iMac 5K > Apple TB3 to TB2 dongle > WD MyBook Thunderbolt Duo (TB1) > mDP to DP cable > Dell UP2716D (2K QHD)
This works perfectly. As a test I threw in a TB1 RAID which should be the weakest link before going to mDP, in my real chain there will be other TB2 RAIDs before it which should work the same.
BTW, the exhaust behind the iMac stand pushes out hot air 24/7, I found it a little bit worrying to leave the TB3>TB2 dongle near the blowout as it has controller inside, so I left the dongle-TB2 cable out of the cable management hole to avoid it.
iMac 5K > Apple TB3 to TB2 dongle > WD MyBook Thunderbolt Duo (TB1) > mDP to DP cable > Dell UP2716D (2K QHD)
This works perfectly. As a test I threw in a TB1 RAID which should be the weakest link before going to mDP, in my real chain there will be other TB2 RAIDs before it which should work the same.
BTW, the exhaust behind the iMac stand pushes out hot air 24/7, I found it a little bit worrying to leave the TB3>TB2 dongle near the blowout as it has controller inside, so I left the dongle-TB2 cable out of the cable management hole to avoid it.
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