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Luffy didn't know when the resentment first started to build.
He had always though of his grandfather as a good man even if they never saw eye to eye. At some point though, that thought started to fade. Maybe it started when Sabo died or when Ace was executed hes not sure.
The first time he really noticed the resentment was only months before he was to set off to the Grand line. It was a quiet day, he had decided to come down from the mountain to hang out with Makino. It was lonely now that Ace was out on his own adventures but he'll see him again someday. Until then he'll be with Makino, the women who practically raised him.
He sat down on his usual bar stool talking loudly to the young bar maid when he noticed just how tired she looked. Her being tired was common but it made sense, she ran this bar by herself, since before Luffy was born. But this- this was a different kind of tired. She looked ready to collapse. "Makino ok?" He tilted his head to the side as he looked down at her. "I'm fine Luffy, it's just been a bit busy" She smiled as she poured someones drink and called out a name. The person came and got it quickly.
Luffy didn't believe her, he's not book smart but he's people smart. He notices everything, always has. That's why he didn't believe her. He noticed that she didn't sleep enough, He noticed that despite being a Monkey D herself she didn't eat like one. He noticed that she was significantly shorter than all other Monkey D's and all D's in general. It's rare for one to be under 6'0 at least. He thought for longest time that it was normal. That she just didn't get the big appetite or height but now he knew that was wrong.
"Kino is lying. She's tired" she could feel her glare at him but at the moment he didn't care. "Maybe she should close down early so she can rest before hunting later" He let his head droop and hit the counter. She huffed at him"You know I can't do that Luffy. I need to stay open, you know how the town gets when that happens. Garp would have a fit if he heard." He scowled, not looking up from the counter.
He loved his Gramps, he really did but the way he treated Makino wasn't right. He treated her like he owned her. Like she wasn't anything more than hired help. But she's not 'help' shes Makino, she's family. It makes Luffy resent his Grandfather just a bit more.
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The next time he noticed his resentment it wasn't towards Garp but Mihawk.
The Baratie was amazing. Everyone who worked there was so funny, the food was great, and he found his chef. Sanji was the best cook he'd ever met and the way he would bicker with Zoro was hilarious to watch. He really liked it there and he hoped to come back another time. Then they were attacked. The Baratie was bashed and destroyed in many way. All because of the solecalled King of the East Blue, Don Krieg. He and his crew had been sent running from the Line by Dracule Mihawk, The Guy Zoro has sworn to defeat.
Their first meeting wasn't pleasant. Not when it ended with Zoro getting hurt ,but it wasn't Luffy's place to step in. It was Zoro's fight. It still pissed him off though. The way he talked down to his swordsman. It took everything in him to not lunge at Mihawk when he saw him cut down Zoro with one slash of his knife. The only reason Luffy hadn't was because Zoro had cried out for him, promising his life to him. That promise, that is what started building his resentment towards Dracule Mihawk.
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The next time it was less resentment and more pure hatred. Though it wasn't just one person. It was for the World government as a whole but especially his Grandfather. It didn't simmer quietly in the background this time. No, everyone could feel the hatred rolling off his body as he fought his way into Impel down. It was especally apparent to Buggy, Mr.3, and Crocodile. When they had him there was none of this hatred. Not properly anways, Crocodile had seen the hatred on Luffy in Alebasta but it didn't feel the same as now.
Luffy incompasitated by Megelian and Bon Clay literally dragged him to Level 5.5. He failed to get to Ace. When Ivankov injected him with hormones and he finally woke up, Luffy was angry, much worse than before. It wasn't quiet any longer, it was loud and boiling. They couldn't get to Ace before he was taken to Marineford.
That anger never went away. Not after the prisoners and himself stole a ship, or crashed into marineford, or when Whitebeard wouldn't let him fight, or even when Ace himself told Luffy to leave. No, It boiled over and burned deep into his soul.
He punched and fought and broke his body just to get up to his brother. Every punch is harder than the last one. When Grap jumped down to fight him the punch that Luffy hit him with felt great to him. Watching his Gramps fall to the ground settled something in him. That resentment and hatred was cemented in him now, he'll never think of him as a good man ever again.
Then Ace was killed, he was killed byAkainu and his stupid Magma fruit. He died to protect Luffy and Garp did nothing. Even though Fleet Admiral Sengoku was pinning him to the ground. He knew his Gramps, he could have pushed Sengoku off him and got to Akainu but he didn't.
Luffy hates Akainu, he hates the Marines, and he despices Garp.
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Luffy's resentment for Germa didn't start as resentment, it started as hatred. They took Sanji from him. They stole his Nakama. He didn't give a shit about them being his family. That didn't matter to him. What mattered was that Sanji was being held captive by those bastards and the Big Mom Pirates.
It didn't matter to Luffy that Sanji had rejected him. Had yelled at him to leave. Luffy decided that he wont move from that spot till Sanji came back with him. Even after he decimated Big Moms Army, and destoryed General Cracker. Even after he was captured and thrown into a book. He tried to get back to that spot. Because where Sanji will be, Luffy promised to be there and he's going to keep that promise.
Big Mom was a cruel woman. She set this up as a trap. She was going to have Pudding kill Sanji during their wedding. Pudding had already shot Sanji's sister. Raiju didn't remember who shot her. Her memories didn't feel right. That's what she told Luffy.
When Sanji's family finally realized that the wedding was a set up and was able to escape the candy prison Parospero put them in, they helped them escape. That's when Luffy's hatred started to simmer down into something closer to resentment.
Hours later when they had managed to get away from Big Mom with the help of Germa 66 and The Fishman Pirates, he had found himself down Sanji. He leaned into his cook's side and let himself settle. He may resent Germa but at least they gave him is presious cook.
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Resentment comes with who he goes against. Even with his family it was prevalent but when he was on the Sunny with his Nakama he could let it melt away with the flowing laugher and joy of his crew.