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-The shop has some useful tools which can make this challenge a little easier. The best IMO are
Blue and Red candle - Allows you to shoot and deal damage from afar without risk
Nightlight - Slows down enemies and tears making dodging easier
Sack Head - Extra bombs and keys plus cards to use ( Heriophant,Emperor ex )
BFF - Your attack flies deal more damage and pretty flies become bigger
Stopwatch and broken Stopwatch
The Compas or The Map
-Bob's brain is actually pretty useful here! Just be careful when using it! Also Guppy's head and Bob's rotten head
-Most of the devil deal items aren't to useful ( except for maybe incubus ) You might even run into a krampus!
-The cube of meat ( or ball of bandages ) can be very useful for dealing extra damage
- Prep your battles, wait until the enemy is not moving or completely vulnerable before going in
- You don't always have to fight, you can use bombs to blast through doors in order to find the boss room.
-If you happen to come by a follower ( Ex Little Steve ) They can make your job a bit easier
It really just requires a bit of practice until you get the hang of it, but the meat cube makes a huge difference in my opinion.
Other advice is, don't worry about fully clearing each floor. Try to find the shop and the boss, and maybe the curse room if you have spare health. BFF (if you manage to find it in the shop) also really helps with this challenge.
My tidbits of advice are be patient, a large part of this is challenge is waiting for your orbital to move into a position to attack, and charging in when your orbitals are in the wrong place will lead to trouble. Avoiding damage should be a priority over dealing damage. Take advantage of flight to hide over rocks and pits where you can. Otherwise Josh's advice is fairly good (Although I find cube of meat/ball of bandages is more of a luxury than a necessity). This challenge is a bit of a trial by fire, where learning to use orbitals offensively is the only path to victory.
enjoy your easy win.
If you have even more you can get either 30 coins or 7 soul hearts. When you spawn Gabriel just walk out of the room and go back in and he will despawn if you are worried you can't take him
I know it's necro but 2024 and I found this post a few days ago when this challenge was kicking my butt