You only need TPMS if you want to restart the clock on when the batteries are going to die. With a 2019, I'd probably risk it and wait to replace them on next set of tires. The sensors will definitely move over from the OEM wheels to the Icons. The tire installer may want you to get the rebuild kits (a couple of gaskets).
I suspect you don't have to worry about the tire hoist mod. I think they changed it somewhere along the way and it wasn't necessary. If you do need it, it's very obvious once it's all in front of you. There is a tube that the chain goes through just above the tire holder where they intersect. If the tube is too long you won't be able to get the hoist through. The mod is to cut the tube off. There are some pictures around, but if you don't find one, it's pretty trivial. I do vaguely remember someone saying that somewhere after 2016 the hoist was a different part and didn't require the mod.
Here's and example: