I am by no means an expert on digital photography or the internet. I was in my 50's before I ever touched a computer. But over the years I have been forced to learn (usually by trial and error) enough to construct a website and take thousands of pics for my auction catalogs.
I think the problem people are having when posting pictures is confusing the physical size or dimensions (e.g. 600px by 800px) with the quality or resolution size (not sure this is the correct term) which has to do with the quality of the picture (e.g. 56.78kb or 3.09mb). The larger this size the longer it will take to load.
The 250kb limit would refer to the resolution or quality not physical dimensional size. Below is a "What's It" from an email from wrenchmensch. The original pic as uploaded measures 900px by 559px but has a resolution size of only 67.78kb. It uploaded fine (but slowly) and shows a picture 250px by 559px. When you click on the small picture the original 900px by 559px is shown.
An unedited picture straight from the camera (depending on the camera resolution settings) can be an extremely large file. Some email pictures I receive can be up to 3 or 4 mb. When I had dial up they could take over a half hour to download.
If the pictures are to be shown on the internet these high resolutions are overkill as the monitors don't display them any better than lower resolution pictures. It would be a different story if they were going to be printed. When I take the pictures for my wrench auctions I save two copies of the pics after cropping and any other editing, one at 100% resolution (for the printed catalog) and the other at 45% resolution (for the web catalog) to save on loading time. I like to keep the web pics around 35kb to 60kb or slightly larger, the physical size is usually around 800px by 600px.
The quality resolution size of the pictures from the camera can be lessened by cropping extraneous areas around the main object, by reducing the quality and dimensional size settings on your camera and by using a plain uncluttered background when taking the pics. Yesterday's newspaper or the kitchen table with the remains of breakfast all add to the resolution size. Also most editing programs such as Irfan View (one of the easiest to use and it's free) have provisions to reduce the resolutions. Even if you use a picture hosting site such as Photobucket the pictures should be edited to speed up the load time and reduce internet clutter. Most of the picture hosting sites also have on line editors. If you use a picture hosting site it seems 690px wide is the max to get a picture to show full size on the page without the slider bar down below the last picture. That[s on my monitor others may be different?
So in short it's not the physical or dimensional size but the quality or resolution size that is not allowing the posting of large pictures. Keep the quality/resolution size below 250kb and large dimensional size pictures will post. Remember picture restrictions are "10 per post, maximum total size 800KB, maximum individual size 250KB" if you are using the board attachments procedure. I guess there are no limits on number of pics if you link to a web picture hosting site.
1930, (or anyone else) if you would email one of the pics you are trying to upload I will see if I have any luck.