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You can get screwed by the RNG, but there's a lot of paths to victory too. I'd say in general you want to head for the boss rooms without a lot of extra exploration especially in the womb and cathedral, but I'd hit the shops in the first few floors; a map or a compass will pay for itself later. And a key for a chest or bomb for a tinted rock/stone chest etc if you are out is usually a good buy. an ehwaz rune or boss room teleport card can let you skip a floor and save you a bunch of cash in the process. A bible would be a great find as much for the flight to get inaccessible pickups as for the boss fights. Even the jump book is a good find. Or one of the activated explosives, etc. And there's a bunch of trinkets... the swallowed penny and counterfeit pennies obviously, but the burnt penny, flat penny, or bloody penny would be good too.
And remember you can go back through doors you've already paid to open, so if you see a tinted rock or a chest but don't have enough bombs or keys to open it you can come back.
...I feel like I may have picked up "the mind" on an early floor in my winning run for that challenge though, so I might not have needed them. I remember seeing the floor plan. I may have bough chaos. Not necessarily a good idea, but a fun one.