Difficulty: Community Vote: 8.5/10
My Opinion: 4/10
Time to Platinum: >100 hours. Significantly less if you already have an advanced save file
Offline trophies: 51 (42 5 3 1)
Online trophies: 0
Playthroughs needed: 1
Missable trophies: None, but Cinco de Panelo is easier to do in a story mission that you cannot repeat
Bugged trophies: None that I know of
Cheats disable trophies?: As demon-like as it is, there's no cheating
Retroactive trophies?: Trophies aren't retroactive, but you can use old save data to get a head start on the leveling process needed before you can attempt most of the trophies.
1. Complete the main story:
Your first goal should be to complete the main story. Make a point to get Cinco De Panelo in the Chapter 3 mission "Board Conspiracy" or it will be much harder to get later. You might as well also get ABC's of Hitting before you finish chapter 4. There are a few others you can get during the main story, but there is nothing else pressing.
2. Level Level Level:
I've made a mini guide here that will give you some specifics on leveling your characters to 9999. It is most important that Mao gets to this point, as the fastest way to get a strong party is by capturing monsters (also described in that post), and your ability to do so depends on Mao. You'll also need a few of your own characters leveled to this point until you can capture the monsters.
3. Collect Illegal Tickets:
After you've levelled, you'll want to begin hunting pirates in the item world. Whenever you defeat a group of Pirates, they will drop an illegal ticket. You can only get 1 per type of pirate. There are also illegal ticket vendors found randomly in the item world who will sell a total of 20 tickets. All in all you'll need at least 34 tickets. Once you have them, complete 35 X-dimension levels to get the Chicken Hat. By now you'll have gotten many, but not all, of the pirate trophies.
4. A monster of a party:
Pass all the stronger enemy bills you can and go to the Land of Carnage item world in the strongest item you have. Get to the floors above 90, collecting items in mystery rooms along the way, and start capturing monsters. You'll need at least ten, some of which should be war slugs. Once you have them, pass all the weaken enemy bills. These monsters should be strong enough on their own to kill everything except the Baal Pirates, so you want to run through high level Land of Carnage item worlds looking for good equipment for them and then level this equipment.
5. Finish the pirates:
Get a weak legendary item to floor 90 in the Land of Carnage item world, exit, and then save. Run the last 10 floors looking for pirates, quitting and re-loading each time until you have all the pirate trophies. The amount of time this takes is based entirely on luck.
6. Buy the Hero Prinny DLC:
Just do it. It's a dollar and it will save you hours of work. Use him to get the 10 Billion Damage Man.
6. (Alt) You're a masochist:
Too cheap to buy Hero Prinny? Then complete the epilogue to get Flonne and use her to get 10 Billion Damage Man. This will take a long time.
By now there are still plenty of trophies left. Each of them deal with some small specific action that would probably never come up over the course of normal play, yet are not that difficult to stage. Follow the steps in the guide if any of them are giving you trouble.
Thanks go out to Attack__Cat who made some good suggestions.
[PS3T Would Like to Thank Lonesheep for this Road Map]