Story and aesthetics I prefer 1 & 2. Their gameplay does get kinda repetitive though and not in a good way. 1 tries to be a very complex game with thousands of elements, party formation and whatnot, but fails to truly explore any of its systems. Or at least the PSP remake failed, never played the og PS1 version. 2 streamlines things a bit, but its mostly just a grindy experience, or if playing the PSP remake of IS, its just pointless random battles that prevent you from listening the cool dungeon music as everything is too easy anyway and I recommend just bypassing everything by using estoma. Also I am one of the few persons that prefer IS over EP, EP has a good cast, but it relies too much on variations of the same events of IS and whenever it promises anything new the result is often just okay at best. It's like the game never reaches its full potential, it rather feels like a regression of IS.
3 onward I just think its too much. I don't hate all anime tropes and whatnot, but I don't really want to go to school and do all that boring stuff and have to listen funny anime banter every single second. If anyone say 2 is anime, then 3 onward are 10x more. At first it can be enjoyable but these games really don't know when to end, often going for 100h+. Being also locked with calendar with deadlines for everything is annoying for me. And I hate how many things they dropped, like now only the main character is able to change his personas because he is this super hyper special person, the extra elements are mostly gone and battles work much more like mainline. That being said even though its less unique, the battle and overall gameplay is much more enjoyable. Also 5 has some really good dungeons, its the closest we got to the dungeon design of Nocturne and DDS era atlus.