This is a general guide that applies to most heroes, and works consistently (at least on normal level).

So starting a normal level game, heroes are not that different.
Their abilities doesn't matter too much. There for sure are stronger ones.
Some heroes with no trinkets and low initial health is icky though (like the Craftsman).
But here is the trinket set that worked easily generally:










If you have not unlocked "Cosmic Petal", try starting with preset dices in slots.
If you do not have the "Puppet", try other discounting items.
"Really Big sword" is awesome but I have never used it on normal.
If you are using "Straw hat", get the Artist
Phoenix Plume is good to have when nothing is unlocked or you have a third slot.

Some basic stuff in-game, try to follow this workflow in every stage

1. Bring the enemies down to one left, focus high attack enemies first.
2. Reduce the last enemy attack to 1 or 2 if possible.
- DO NOT FOLD IT YET-
3. Keep tanking while rolling, until you fill the Gold Coin set every stage!
4. Ready you and your companion's ability in the process.
5. Fill your dice slots with different dices you think you need the most.
6. Fold the final enemy.
7. Do the same next stage.

!! Do consider if tanking is worth it sometimes!!
I would say even 10~15 health left going to the next stage is pretty safe.
So, even when the dungeon master is out, let it out for a turn doesn't hurt.

The big turnoff is Boars and Rats, they have high attack. So if you are not happy, restart!
Aim for anything that has a attack of 1.

Think about how easy can you trigger the item and synergy with your hero/companion's ability.

Getting more items usually helps.
Which is why the -1$ trinket is helpful, it gives you a lot of flexibility and more options. It might help you a bit better in early game. However, in late game, Really Big Sword is more efficient, especially in hard and extreme mode.

Generally

• Don't go for items that has negative effects. It might easily mess you up.
  
• Go for items that brings you Coins or saves you money, if it triggers easily and often.
  
• Go for items that brings you colored dices and more dice rolls.
  
• Go for items that heals passively, especially if your HP is low.
  
• Otherwise, save money.
  
• Items by percentage are fairly good, buy it only if you are wealthy.

In mid to late game and prior boss fight

• Go for items that has negative effects, if it is useful in anyway.
  
• Prioritize on getting more dice rolls or colored dices.

Again, think about use frequency and synergy
Don't waste money just to buy something that seems good but doesn't work with your skill sets.

Unpopular opinion, my companion selection:

Prioritize and make sure to activate their skills EVERY STAGE (even if you have to lose some extra 1~3 HP, still worth it):

• Peasant (try only putting 6)
  
• Shopkeeper (possible free item)
  
• Treasurer (not the best)
  
• Artist (one of the best)
  
• Beggar (make sure you have 5 silver coins when you use skill).

Game ending for fun:

• Scribe (make sure you activate before last shop and if you are rich)

Early solid picks:

• Seducer
  
• Princess (weaker but sometimes not awful)

Seems strong but not really efficient:

• Healer
  
• Bard
  
• Guard
  
• Spy
  
• Monk
  
• Cook
  
• Fisherman

Seems not that strong but actually fun and works:

• Gambler
  
• Seer
  
• Wanderer
  
• (These companion's skill can be used unlimited in a stage, so you know with the things you can do with it.)

The only bad companion to me is the the Advisor

If you do it consistently by the time you reach boss room, you should have:

• Enough HP to tank some damage with your companion.
  
• Enough dices to deal with various situations.
  
• Enough items to help you deal with damages and defense or healing.
  
• Boss fight is when the ability matters, so might as well have it ready beforehand.
  
• Make sure you fill your dice slots before coming in.
  
• Boss is random up till "warlock", after that, it is simpler. But with good timing on when to pop your ability along with your companions, normal bosses are not too bad.

Hard mode is slightly harder than normal, but the basic game flow is the same. This is when you should start thinking about heroes ability and the timing.

It also applies to endless mode. In endless mode, some heroes are much easier than others in deeper stages. Yet, the opening is not much different.



However, this sloppy mechanic wont work in extreme, but with some adjustments, extreme is not that extreme. Some heroes can still cruise through with the right trinket picks. But this is a lazy guide, so that's all.