The Single Player portion of this list is mostly straight forward, due it's very progression based nature.
Although this includes a handful of trophies awarded at certain points in the main story, a large section of the list is catered towards tasks that are also required for the "Redeemed" trophy, for attaining 100% in the single player game completion statistic.
It's a typical Rockstar requirement, and going through the checklist is just long more than anything. A few of the more challenging aspects come from the Single Player ambient challenges and fulfilling the requirements in order to unlock the rare outfits, and in total, you're most likely looking at around a solid 30-50 hours to achieve 100%, so it's a typically hefty slog which will keep you occupied throughout the rest of the Single Player trophies, which will mostly be earned along the way as you complete individual aspects of the 100% checklist.
Aside those, you still need a collective total of 1750 kills using a variety of weapons, including rifles, pistols and cannons, but this can be done across all game modes, so it's probably best to work towards this online if you still don't have the relevant trophies from the single player venture. However, the "Mowing them Down" trophy, awarded for killing 500 enemies with a mounted weapon, is best done by just replaying missions that require use of a mounted cannon, rather than going online and just tediously trying to accumulate kills, which can be an extremely long process.
The "Spurred to Victory" trophy probably deserves a mention too, which requires you to complete 20 story missions without switching to a new horse at a hitching post. This means the horse can't die, be lost or changed at any point for 20 missions, and given the fact it may also be glitched could cause you go back for a second play-through, as I had to, so it's probably best to knock it off as quickly as possible but also ensuring you keep the horse safe at all times.
It is also important to note that there are only 57 main story missions, so breaking the streak enough times will ultimately cause the trophy to become missable, and you'll have no other choice than to restart the game and try again, which is quite a large inconvenience for just a solitary trophy.
The "Unnatural Selection" trophy, awarded for killing one of every animal species in the whole game, requires you to kill all 27 types of creature in the game. Some are alot harder to find than others, and will make you search various areas for hours trying to find them, so a huge element of patience is definitely needed for this trophy.
There isn't much else worth noting, but there are some cleverly creative trophies, despite that fact the "Manifest Destiny" trophy, awarded for killing the last Buffalo in the Great Plains, felt like searching for a needle in a haystack at times.
The Multiplayer portion is where the game throws up some more difficult challenges, including "The Quick and Everyone Else" trophy, awarded for winning 3 public matches in a row, which does actually mean you need to be the best performing player in the lobby for 3 straight games, which is by no means easy. This trophy also relates to Free-For-All game modes, which means you don't have the luxury of just being able to hop into team games and hope you come out on the winning side, which means you'll need to plug your own work into this challenge, which is tough.
The "Go Team!" trophy, awarded for winning 4 team matches in a row, falls along similar lines. It's easier to win as a team than it is individually, but just make sure you've got a skilled team who are committed to winning, and this one should come sooner rather than later. It's also better to try and stick to the same lobby without backing out, otherwise you run the risk of being thrown into a game in process, where you're placed on a losing team, and thus, upsetting your streak.
The "Have Gun will Travel" trophy, awarded for completing all hideouts in a single public free roam session, will see that you need to put in about 3/4 hours of completely uninterrupted gameplay to achieve. This means you can't afford to leave the game or be disconnected from the online mode at any point, and since the trophy requirements need to be fulfilled in one session, you'll have to start all over again if this occurs at any point. It's hard enough having 4 hours spare, but even harder if you cannot complete them in a single session for whatever reason.
Despite all of this, the main focus of the Multi-Player mode is the "How the West Was Won" trophy, awarded for reaching the top rank for Multi-Player experience. It isn't as gruelling of an experience as the "Wanted" trophy was in GTA4, mainly because the online experience is much more enjoyable and grief-free, but there's still a solid amount of dedication required in the very same way.
Trying to achieve alot of the DLC trophies simultaneously made ranking up much more enjoyable, thanks to extra variety the DLC bought to the game, and being able to capitalise on a 4x experience weekend allowed me to go from level 40 to 50 within around 3/4 hours, which cut hours off the regular completion time, and definitely helped nudge the rating down slightly from my initial impression of 8/10.
Regardless, along with the 50-odd hour Single Player contribution, you're probably still pushing towards an 80-100 hour Platinum with everything taken into account, so there is definitely a slight grinding element too if you cannot take advantage of the increased experience events. Mix the time consuming nature with some genuinely challenging trophies, and this one has a tough layer to it.
Notable Trophies -
How the West Was Won
Reach the top rank for Multiplayer Experience
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