There are two kinds of metadata involved when you consider jpeg or other image file.
One is the file data. This is what the Finder shows. This tells you nothing about the contents of the file, just the File itself.
The problem with File metadata is that it can easily change as the file is moved from place to place or exported, e-mailed, uploaded etc.
Photographs have also got both Exif and IPTC metadata. The date and time that your camera snapped the Photograph is recorded in the Exif metadata. Regardless if what the file date says, this is the actual time recorded by the camera.
Photo applications like iPhoto, Aperture, Lightroom, Picasa, Photoshop etc get their date and time from the Exif metadata.
When you export from iPhoto to the Finder new file is created containing your Photo (and its Exif). The File date is - quite accurately - reported as the date of Export.
However, the Photo Date doesn't change.
The problem is that the Finder doesn't work with Exif.
So, your photo has the correct date, and so does the file, but they are different things. To sort on the Photo date you'll need to use a photo app.
Now things get more complicated:
My photos are not just coming from a camera, they also come from FastFoto FF-640 scans.
Most scanners do not create images with Exif metadata. And while in Photos you can edit the date that is only in the database, when you export there is no place the file for the app to write the Exif metadata.
Multiple photos makes no difference. There's no way to do what you want. The workaround most people use is to put the date in the title like March 18 18, John's Wedding... or something similar.