No issues, you guys did a splendid job with just a few questions. Happy to answer 
Yes, a lot of same name files did come like this. Missed file instance only happened when multiple images or files were named as “Image from iOS (# some number; say 17, 18, 20)”. I had to manually download, change name and copy in my folder. I have attached an example folder here – where you can see a lot of such images where I manually added some character to have a different name before moving to the folder.
By the way, during the process, I got to know that I can just add a new file to any local (desktop) slack folder and odrive will automatically upload that file to corresponding slack channel – which is awesome !
Sorry for late reply. Happy to help.
Thanks.
