1. Auto-rotate is a feature of the camera, not iPhoto. iPhoto creates a preview of the shot on import that features the rotation. It's on the camera that you disable rotation or rotate the photo before bringing it to iPhoto.
2.
I need to preserve the "file created" date and time information for record keeping purposes.
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. 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. Trying to sort photos on file data is a waste of time. It will always break down at some point.
3. Not sure what you mean by this
I am moving images from my iPad to my MacBook Pro using iPhoto, since the MacBook Pro does not recognize the iPad as a device.
but have you explored Image Capture (in your Applications Folder)