1. Challenge #17 & 18 for death’s touch and tech.5 and 14 for SMB

2. Isaac to the foot (unlock Azazel on the way by taking 3 devil deals)

3. Defeat Mom’s Heart w/ 5 Different chars in a streak 5 times on Normal, then the remaining runs with azazel till 11 total

4. Kill Isaac and Satan 5 times each with Azazel on Normal

5. Do Isaac to The Lamb on hard w/ Mega Satan if possible

6. Do Azazel to Hush on Hard

7. Do Blue Baby to the chest on Hard to unlock the D6 w/ Mega Satan if possible

8. Do Eden to the chest on Hard to unlock Blank Card w/ Mega Satan if possible

9. Do the Demo Man Challenge (#9) to unlock Chaos Card

10. Do Challenge #2 to unlock Jera

11. Do Challenge #6 if unlocked

12. Do Greed Mode once with each character donating as much as you can. When finished doing that do it again with the ones that donated the least until you unlock Keeper. If you have a lot left to donate you might want to use the Glowing Hourglass/Chaos Card/recharge item trick.

13. Beat Challenge #15 for Swallowed Penny Unlock?

14. Beat Challenge #22 for get out of jail free card

15. If Mega Satan done then do challenge #19 to unlock Epic

16. Do all of Lost and Keeper’s post-it note on hard.(if the Missing Poster pops up, make sure to kill yourself on a sacrifice room to unlock The Lost; otherwise you’ll likely need to do a mini-break with Mom’s Trinket Box to do so)

17. Do all the Post-It Notes, then rest

18. Do challenges 16, 28 and 29/30 (29/30 are bugged and swap unlocks randomly) challenges to unlock the items.

19. Unlock D4 by blowing up 30 slot machines

20. Unlock Small Rock by blowing up 100 tinted rocks (probably done at this point)

21. Unlock Little Gish/Steven/Little Chad by killing their respective bosses (which all require unlocking)

22. Unlock Scissors by dying 100 times

23. Unlock Parasite (probably done at this point)

24. Unlock Super Bandage by doing the Super Bandage Girl achievement (Restart as Lilith for b1 Horseman that drops bandage ball) You can/should probably do the Super Meat Boy achievement this way as well if you didn’t do it during Lilith’s Greed mode run.

25. Do a breaking run to touch all remaining items.

26. Play the shell game 100 times.

27. Do all remaining challenges.

28. Spam Eden tokens at the very end of your savefile, and hopefully pick up a lot of the problematic items.

A lot of the smaller things are variable and are done in no real particular order.