If you don't have full health when entering a floor you have an increased chance for an aracde to spawn. Lucky Foot raises the chance you'll get stuff while gambling (skull swap game has a 55% chance of winning with Lucky Foot for example), blood donation machines will give more coins and are much more likely to explode into Blood Bags (meaning running out of money is almost impossible), and fortune tellers will always give you either a soul heart, a trinket or blow up- Use that to your advantage by taking devil deals and stacking up on soul hearts from fortune tellers, that way you'll have good items from the devil deals (Pact, Brim, Mark...) and still be healthy enough to keep going. Devil deals are much more likely to appear if you don't take red heart damage on the floor.
Also when you know all pills are good it makes items like Bottle of Pills and Safety Cap much better to use. If you happen to find Dead Cat early on you can farm bosses with it by beating the boss and killing yourself in the boss room with a bomb so the boss will respawn for more items.
Don't let the game break you, let Cain break the game.