Hi,
My take:
1. If condition means the situation in which people live or work, especially the physical things that affect the quality of their lives OR the state that something is in, especially how good or bad / how healthy one is - then the two sentences are fine and mean similarly. However, 'What' is often used if one does not know the listener's past history; while 'How' is used in reference (comparing) to the listerner's past condition.
2. If condition means something that you must agree to in order for something to happen, especially when this is included in a contract - then the second sentence sounds odd.
Best wishes,
Hoa Thai