Looks awesome. The nurse of the year looks like the border didn’t close up properly, and it should. Did the paper shift while plotting?
I agree, you are ready to get it dirty. Just take it slow and try to keep your confidence with some simple projects and be ready for some mistakes. Test small pieces before going onto a large, expensive piece of wood.
Estlcam has a “cut order” field for each piece, so you can set the cut order there.
If you set up cuts using more than one tool, Estlcam will determine that you need a tool change, and will insert your tool change gcode into the CNC program. It can do this automatically, and is reasonably good at minimizing changes, but it can still mean changing back to a previously used tool if you do not specify the tool path order.
There is a “tool change” section where you have to put in the gcode commands to do the tool change. You will need to add whatever code you need there, including finding the Z origin again.
I have had success with tool change operations, but I’ve found it far easier to just do each tool as its own file. Cut all of the job that needs one tool, and then all of the job that needs the second tool. This way, you can take your time with the tool change, and re-home the Z axis as many times as you need to.