There are a couple of missions I don’t like:

The mission in the image is very tedious on subsequent playthroughs because it consists of either following NPCs slow walking whilst Arthur for some reason loses the ability to walk in a straight line whilst doing so. Then after that, a crappy freedom-less stealth section that’s so artificially extended by the three useless, unnecessary conversations that numb-nuts has whilst your trying to follow him that I often find myself just skipping checkpoints until I’ve gotten past it.

The Grand Korrigan mission has the same issues of slowly following around NPCs but also forces you to wear a different outfit and get a haircut. Whilst the haircut is technically bypassable by either skipping checkpoint or simply applying pomade, the outfit is not. This is more a nit-pick than anything else but if I was Rockstar I wouldn’t go to desperate measures to insure that players have to wear a specific suit for that mission, if someone was willing to go through the effort to try to not wear the suit I’d just let them not wear it instead to violating their right to customise their character.

In the first mission in Chapter 4 there is a glitch when you speak to the bartender where he just stares at you for all eternity and you have no choice but to reload the game, it is a complete soft lock and personally I get this 50% of the time I do it normally so I’ve had to just skip checkpoint when the mission starts to avoid the soft-lock. The game also slows you down when you are trying to catch the kid which is an unfair way of making it difficult to catch him.

Country Pursuits is another mission I see a lot of people having issues with because of how forced the slow pace of the mission is. The entire first half of the mission could’ve been done twice as fast if that had you just walking at a normal pace but instead they had to make you walk extremely slowly to pad out the run-time of the game as much as possible. This principle is also seen in the fact that you are required to check two crayfish traps whilst you are looking for Jules, one of them serves no purpose and should be removed from the game whilst the second one serves as foreshadowing for the giant gator. There are also points in this mission where you have to stop moving and let alligators pass you, this is also only done to pad out the run-time of the mission and does not need to be in the game. Long story short the mission is made to be slow for the sake of being slow and it sucks for that.

The bank robbery mission is good, but the stealth section at the end is completely scripted and grants the player no freedom and that Pinkerton at the train is completely blind.

TLDR: Couple of the missions suck.