Thank you guys again for all the help!
I ended up doing the DSG DMF swap this weekend with the help of a friend, it mostly went smoothly and was not terribly difficult.
Tips:
There is a HIDDEN bolt where the starter goes in that you have to pay attention to, this is there once you remove the starter in the top hole. It is an 18mm bolt I believe.
Don't dawdle about removing the subframe, (just remove it already.......), I did and it was practically hell to remove the transmission with the subframe in. You can remove the subframe easily and once that is done then you have to remove the passenger side control arm, also very easy to do. Help is key in doing this but will save you hours in frustration. You will also have to remove the transmission mount from the transmission itself, four bolts on bracket and three on the mount itself. This will give you even more room to maneuver the transmission out.
I removed the pilot bearing which stays inside the engine. It was a HUGE pain in the butt. Borrowed tool to pull it out from parts store but it just stripped the bearing. I do not recommend you use the tool, you will see it only has two prongs. Had to buy one at Harbor Freight with three prongs and it sort of worked but would not fit into the hole initially without a lot of work. I recommend you get the right size VW-specific tool if you are going to replace this.
Also, perfect time to replace the rear main bearing if you are worried about its longevity. I was going to do so but part was expensive and not readily available locally.
It is not a huge job but you definitely will want something to steady the transmission once you are ready to lower it, we used an old transmission floor jack and it was unsteady but it was necessary. You can probably use a normal jack but it will be even more unsteady.
Once you are done with testing everything, I recommend doing a DSG adaptation with your handy VCDS Vagcom. This will ensure the transmission knows the difference in DMFs and such.