Even though your heroes level up, the level itself doesn't make them stronger. Stick to apprentice level dungeons in each area. You can usually make up the cost of the provisions in one or two battles, and heroes are free.
It's very difficult to go completely broke sending level 0 heroes at apprentice dungeons unless you're party wiping every single time. There are guides if you want specific strategies for each area, but just experiment. As you understand the different enemy compositions in each area, you can start building sensible parties to tackle those challenges. Best overall strategy for a newcomer - launching fresh stagecoach meat at dungeons to work out what each of the classes can do and what abilities you wish you had to face enemies.
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