For those who do the trophy cleanup at a certain point, do you start with the hardest/rarest trophies first?

[Feral]

Usually go for whatever trophy is closest to completion regardless of difficulty or rarity. 

[Lava_Yuki]

I use a trophy guide and get all the story and missable ones first. Once post game comes around, I definitely go for the quick and easy ones, and leave the hard grindy ones to last. I also keep an eye on ones that can be worked on naturally whilst playing the game, like collectibles. I leave the longest and most time consuming trophies to last

I tend to avoid games with online and multiplayer trophies. 

[AJ_Radio]

I consort a trophy guide for any missables, then I focus on the story and afterwards I do cleanup for what I have left. 

 

It also helps to keep an eye on anything that is known to be glitched, and that you make backup saves just in case. 

 

One trophy glitched on me in Castlevania Requiem: Symphony of the Night & Rondo of Blood and I had to spend three hours to do a second playthrough.