In the past I've used a photo resizing app on my iPads to make images come in under the 300kb site limit. But for some reason that has been highly inconsistent recently, only once in awhile successfully attaching an image, in spite of them meeting the kb criteria. The app itself still works, although it has become aggravatingly more complicated. You might check your source for apps and try to find one that you like; there are tons of them, many too complex are costly. Many years back, Steve and I created a document designed to help members resize and post photos here, so you might want to check that out under the General Board > Forum Assistance (Members Only).
All that said Randy, in case you are using a MacBook perhaps this will help: click on the "Preview" app commonly found in the Dock at the bottom of the screen (it looks like an upside down, black bottomed shot glass). Locate and open your photo; click on the Tools menu at the top; choose Adjust Size and Resample image; enter a smaller pixels/inch value in the Resolution field so you get below 300 as it calculates kb in the Resulting Size section. Given today's hi-res cameras, it may take some drastic percentage downsizing to do the job.
Be advised I've admittedly not actually tried submitting images here using the above described method, but am operating on theory alone, so if you try it let me know how it works. The Preview app for iPads/iphones is similar, but may not calculate resolution reduction in kilobytes as you go, so more guessing is involved - trial and error until the image's information (circled i icon) window shows its under 300kb.
-Joel
