This was my line of thinking when I did my 3rd playthrough. My order wasTo me, this is exactly the reason why on my next playthrough I'm going to do Skellige first before Novigrad. That way Geralt can sort out his feelings with Yen first before heading back to let Triss know.
Triss' first personal quest
When the Brothers in arms quest unlocked I did now or never
Doing the quests in this order allowed me to make sense of Triss not showing up in Kaer Morhen and made up for the lack of being able to mention being in a relationship with Triss (because I wasn't in one at this point) and made things go a bit smoother (up till the Battle of Kaer Morhen then the inconsistency kicked in until the end).
Still though I don't think it should be the player's job to make sure plots of a game flow properly (like the Triss romance).
They could have just held off on being able to do Now or Never until after the Ugly Baby quest but I would prefer if they just allowed the romance to be recognized if you did it beforehand.