Yes, the size is important, but it's not the photo size (though that can have a bearing on the file size). It's the file size. If the photo file is larger than 299K, the server will stop uploading without even giving a message, it just hangs. I don't have a way to put out a message on that.
A lot of camera software defaults to extreme file sizes. Usually a photo that you are going to render on the net, need have a file size no larger than a 30 or 40K to get acceptable resolution (given the size of the photo we can fit in a post). In fact we shrink the file size even more to store it.
Usually you can use a tool such as MS's paint program on Windows, Preview on the Mac, and Gimp on any of those or Linux/Unix. You just load the file in and save it. Those programs will tend to save more realistic sized files than the programs provided with cameras. Of course, some of the camera software will give you options to lower the file size too. With a jpg file, it will usually be a "quality" setting. Don't worry, it doesn't actually hurt the quality since the quality is far to high for internet consumption anyway.
But you may find the file size is 500K, 1MB, or I've even seen some photo software store a 3MB file for a simple picture. There is a reason they do that, but it doesn't apply when you are uploading the picture to the net.
If all else fails, just email me the file and I'll shrink it. Anytime is fine except for late evening. My farm net gets clogged from 7 to 12 or so. Address is support at ytmag.com.
I know this is long, but there is one other possibility. If you upload on Classic, it stores the photos to tractorshed.com. Some security software will block accessing tractorshed if you post from ytmag. I have a new technology I'm going to implement to make sure that doesn't happen (it's called AJAX for those interested), but I haven't done that yet. It's improbable that this is the problem but it did happen to someone a couple of years ago.
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