So I wasn't exactly where I should post this, but it has come to my attention that the default parameters for messaging here do not do 2 important things
1. display messages as a conversation
2. keep a copy of a sent image in your inbox/thread
This has lead to issues with some of my recent trades/purchases, so in the interest of greasing the wheels of business please find the guide below
In order to change this, follow these steps one time
First- click Profile -> Account settings
Second- Click Modify Profile -> Personal Messaging
Finally- change the Display personal messages drop down option to "As a conversation" and check the box for save a copy of each personal message in my sent items by default
AND CLICK CHANGE PROFILE in the bottom right