How Much Should Your Photographer Think For You?
( tl;dr: Ask your website developer for an optimal image size in kilobytes; then share that with your photographer )
When shooting for an ad agency, I would never crop too tightly, sharpen very much, or compress an image. The expectation is that someone downstream from me is going to do additional work on the file, and that professional will expect some latitude to work with.
Expectations are different with our corporate clients. The file I send will very likely be posted to a website immediately, exactly as I sent it. The expectation in this case is that the file we send should be ready to use, as-is.