Re: Possible way to upload image to post
I think rather than attachments you want the “Allow Images” plugin, where people can insert an image into their reply.
https://bbpress.org/plugins/topic/allow-images/#post-6
The member has to have the image hosted somewhere accessible on the Internet though ( http://imageshack.us/ or http://photobucket.com/ or http://flickr.com/ or something ). If you want the ability to host their image then display it rather than link to it as an attachment, then you might want to look into this alpha version of the attachment plugin that allows inline image viewing.
https://bbpress.org/forums/topic/priority-1-imagefile-attachments#post-17539