Welcome to the forum. The Chesapeake can get pretty rough, but as long as you watch bay conditions, you shouldn't be too bad with it. 24 foot is about as small as I'd want to go on the bay. Our first boat was a 24ft sea ray sundancer (little heavier and probably could handle a little more than a bow rider same size). We took that boat all the way up to the C&D and as far south as Crisfield.
I had a 246 Cuddy here on western Lake Erie. Our chop here is very close together and most of the time does not have any sort of direction to it. I never felt unsafe on a rough day but it beat the $hit out of you. We couldn't exceed 25 - 28 mph most of the time. The boat was just to light and not long enough to stretch the gaps between the chop. That boat measures 26' over all but really only has about 22' of the bottom in the water. Don't get me wrong it was a great boat you just had to pay attention to the weather and take your time.
I'd go out in waves up to maybe 2 feet. I'd put cargo up front and passengers at the stern, because the ride is always smoother at the stern.
If you get caught in 3-4 foot chop, you'll be safe, but you and your passengers will hate it. You'll have to slow down to 7-10 mph, and everybody will get soaked.
@asledz1756 If you are thinking of a different boat I recommend a power cat. I had a 22 ft Sea Cat and I had it out in 4-5 ft seas and never got wet and still do about 25 mph.
Answers
Dream 'Inn III -- 2008 400 Express
That boat measures 26' over all but really only has about 22' of the bottom in the water.
Don't get me wrong it was a great boat you just had to pay attention to the weather and take your time.
If you get caught in 3-4 foot chop, you'll be safe, but you and your passengers will hate it. You'll have to slow down to 7-10 mph, and everybody will get soaked.