Follow water from the roof to its destination.
Look at roof planes, gutters, downspouts, extensions, drains, slopes and discharge points. A downspout connected to a pipe is not enough; the useful question is where the pipe ends and whether it works.
Visit or revisit the property during wet weather when possible, and compare visible conditions with the seller disclosure and inspection.
Treat the crawlspace as evidence, not a scare tactic.
The inspector may identify standing water, staining, damaged vapor barrier, organic growth, plumbing leaks, pests, insulation conditions or wood deterioration. Findings should be interpreted in context and referred to qualified specialists when needed.
A dry crawlspace on one day does not establish year-round performance, just as a moisture observation does not automatically establish the source.
Budget for correction and maintenance separately.
Cleaning gutters is routine maintenance. Regrading, drainage design, foundation repair or chronic groundwater management can be a different category of work.
Ask contractors to define the observed problem, proposed remedy, limits of work, permits if applicable and what outcome they will stand behind.