>>36479178>>36479230The most challenging mainline games have been DP, gen 5 (especially challenge mode BW2) and USUM (which fixes some of the battles so they work as intended), while the easiest were gen 2 and 6 (in both cases due to poorly implemented level curves).
Gen 1 has artificial difficulty based on a level curve that's poorly implemented in the other direction. Gen 5 and gen 7 try and use intelligent AI and difficult Pokemon. DP was more difficult than Platinum because originally they gave some of the "type-theme" gym leaders and E4 differently typed Pokemon to mix it up (like Flint having a Lopunny, Drifblim and Steelix), but they wimped out of that by Platinum and went back to monotyping for all except for Cynthia.
So, there's not really any clear downwards curve in terms of difficulty.