Check the roof itself
Walk the yard and look up at every slope for lifted, curled or missing shingles, since these are the shingles most likely to fail outright in the next round of high wind. A pair of binoculars from the ground catches most of what matters without needing a ladder.
Flashing around chimneys, skylights and where a lower roof meets a wall should be checked for gaps or loose sections, since these are common entry points for wind driven rain even on a roof that is otherwise in good shape.
Check the gutters
Clogged gutters overflow during heavy rain and send water down the fascia and siding instead of away from the house, and a summer thunderstorm in Richmond can drop more rain in twenty minutes than a gutter clogged with spring debris can handle. Clearing gutters before storm season starts is one of the cheapest things a homeowner can do to prevent water damage.
Downspout extensions should be checked to confirm they are still directing water away from the foundation and have not been knocked loose or buried under mulch since last season.
Check the trees nearby
Any limb resting against the roof, any branch that looks dead or has lost its bark, and any tree leaning more than it did last year are all worth a closer look before storm season, since these are the failures most likely to cause roof damage during high wind. A quick prune now is far cheaper than an emergency removal and roof repair after a storm.
After the storm passes
A quick walk around after any severe storm, checking the yard for fresh debris and the roof for anything new, catches most damage early. Waiting until a leak shows up inside the house usually means the damage has already spread further than it needed to.
Building a simple seasonal habit
Two checks a year, once before storm season begins in spring and once after leaf drop in the fall, catch the majority of problems before they turn into interior damage. Neither check requires climbing onto the roof personally; a pair of binoculars and a walk around the yard covers most of what matters, with a professional inspection reserved for anything that looks off.