I'm getting an error that says it needs to be jpeg, which it is and its not allowing me to upload/attach pictures. Anyone know what the issue could be?

Some issue with the website but the way around is to use this site

https://postimages.org/

You'll want to first pick default then 1600X1200 picture size and then no expiration. From that point click choose image where you pick which picture you want to post and it will give you several links but you only want the "Direct Link". Copy and paste the direct link URL into the "enter an image" which is at the top of the Post box on VA Gun Trader posts (looks like a sunset with a tree).

That's how I went around the issue. Hope this helps!