So i figured it out, I think! It may had to do with the way I was creating the Image. I was having issues where I created the image via on-demand, it kept saying computer was not registered. Even after I installed toec.exe and approved the pc in theopenem web gui and runing the .\toec.exe --prepareimage on the computer with the image i was uploading. This maybe due to the fact that i didnt Collect Inventory or Force Check-In.
Once I did the Collect Inventory and Force Check-In and got all the data to load in from the computer I was able to successfully create the image via the exesting task and I was able to Deploy the image with out having this "Error Determining HD Size Required".
Hope this will help anyone having this issue like I was.