Wow the keeper is not fun to play.
Tips for Keeper:
1) Always leave pennies lying around. They're more important for your health than they are for buying things.
2) NEVER take a 2 heart deal with devil.
3) If there's a 1-heart deal with devil, only take it if you immediately have a Strength card or other HP boosting item (health down pill, Breakfast, etc) available.
4) Curse rooms ARE NOT WORTH IT.
5) Re-rolling Lost-style is encouraged (until your first item room gives you something decent, B or A tier items).
6) Swallowed Penny >>> All other Trinkets. If you can get Smelter, then you're pretty well set.
7) Blood donation machines should only be used if you have PhD, and even then, carefully. Swallowed penny + Blood donation machines will help a lot as well.
Since several of those are up to luck/re-rolling, I'd agree that the Keeper is not really fun.