Uploading Pics?

I want to start more threads on my build with pics but the way I do it for me its a PITA. If I did a thread with out pics that guy would put that little train of captions of this thread is useless without pics and I would have to agree.
My main problem is when I am making a post and use the manage attachment button the top box with the files to drag and drop wont clear the old pics it says photos not utilized in one hour will be deleted they wont go away. The pics I upload are from my blackberry and all have very similar names and i often post the wrong pic and have to edit. If I could delete the ones I'm done with and upload the next set I wouldn't have to go back and forth to my pics and look at the file names.If its easy I will do it Ill be the first to say I'm no computer whiz and I have no patience for thing that don't do what I want I just wont do it?