'Picture not showing up on FB, only the URL

after reading through the other posts, it appears this (or issues similar to this one) has been a problem for a few months- does anyone know if it’s been fixed? Do I need to uninstall/re-install Jetpack? I just updated it today.

When you share a post on Facebook, or when Jetpack Publicize publishes a post to your Facebook page, Facebook crawls the page and looks for Open Graph meta tags in the head to build a complete post preview (with an image, title, description, …).

You can see what Facebook sees by entering one of your posts’ URLs in Facebook Debugger:
https://developers.facebook.com/tools/debug

Jetpack automatically adds these meta tags to your posts, so you don’t have to do anything more than you’re doing today.
Looking at the post you mentioned earlier, it includes 4 image meta tags, all larger than 200x200px (the minimum size per Facebook requirements):

https://thecookerymaven.com/wp-content/uploads/2013/12/DSC_3905.jpg
https://thecookerymaven.com/wp-content/uploads/2013/12/DSC_2998-2.jpg
https://thecookerymaven.com/wp-content/uploads/2013/12/DSC_8920.jpg
https://thecookerymaven.com/wp-content/uploads/2013/12/DSC_8916.jpg

Yet, Facebook seems to think the images are not large enough:

• https://developers.facebook.com/tools/debug/og/object?q=http%3A%2F%2Fthecookerymaven.com%2F2013%2F12%2Fwisconsins-northernmost-sugarbush%2F
• https://i.wpne.ws/Sng6

That’s unfortunately a known Facebook bug. I would recommend that you add your vote to this bug on Facebook bug report platform:
https://developers.facebook.com/bugs/483025408453290

I’m afraid there isn’t much you and I can do at this point: you’ve done all you could do by providing Open Graph meta tags for each one of your posts. It’s now up to Facebook to use these images or ignore them.