When I was younger, I received Pokemon Ranger for the Nintendo DS as a Christmas gift. I wasn't really thinking about playing it, but after a while I decided to give Pokemon Ranger a go. Pokemon Ranger has been one of my favorite Pokemon spin-offs of all time, it had a great story and a new refreshing style of play that I've enjoyed as well. In terms of difficulty the game was relatively easy. However, the last boss Gordor, leader of Team Go-Rock Squad was very infuriating. Gordor had gotten control of the Legendary Beasts-Raikou, Suicune, and Entei. The goal was to capture all three Legendary Beasts to free them. The most infuriating part about all of this is the legendary beasts were able to break your stylus in a matter of seconds.
Raikou would run around spawning lightning bolts everywhere you were going to capture it. Raikou moved in very sporadic movements so you could never really predict its movements. This was frustrating since you had to battle all 3 legendaries one after the other, without your Capture Charger not at 100% usually near 70% or so.
Suicune came next into the fold, Suicune also was just as irritating if not even more irritating. Suicune would spawn clones, shoot aurora beams, and like Raikou would move very sporadically while also disappearing. It was infuriating because the clones that Suicune spawned could damage your stylus, if you accidently attempted to capture a Suicune-Clone, it would backfire badly as the real Suicune would shoot an Aurora Beam right at your capture loop. I think one of the most annoying moments in battling a Suicune is the fact that Minum's ability wasn't as effecitve as it normally is(even on a water-type). I was close to capturing it while it was shocked but it would disappear quickly and multiply afterwords, repeating the process over and over.
The final boss, Entei, was the most infuriating part of the game. I had to re-battle Gordor repeatedly, because everytime I beat Raikou and Suicune I would get absolutely destroyed by Entei. Entei's attacks caused flame to border around the screen. This became very problematic as the space that wasn't engulfed in flame was where Entei ran around. Entei,not only broke the capture loop, but also dealt more damage on the Capture Charger than Raikou and Suicune. Entei was always impossible to capture and having to restart and go through the entire battle with Gordor and the Legendary Beasts became very irritating. This was a very annoying battle and one of the most infuriating moments I've experienced in a Pokemon spin-off.