I hope I follow and address your concerns. I have and love the Lutron Caseta Products. I have used them for a few years now and just recently upgraded my Hub Pro v1 to the new Pro v2 which allowed Homekit. The process I took based on my knowledge of Caseta and some input from Will from Simple Control was this.
Setup the Hub from Lutron and all the devices first. Create Rooms, Scenes, Schedules on the App (hub) to control everything via the Lutron App. In the App enable the Integration and send yourself the report via email. This provides you will all the ID’s of all your devices for use later in SC.
Once you are all setup and happy with this turn on, link Lutron to Homekit so now you have control of the Lutron Devices via Homekit.
Now you can go into Simple Control and turn on Homekit this will pull in everything you have in Homekit into Simple Control and add it to the Home Bar for quick access.
The tricky part I found was adding commands into activities for control over Lutron Devices. What you have to do here is add the Lutron Hub as a Device again to SC this will now allow you to add commands to activities to turn on a light or off a light and or set it at a brightness level. You can also then adjust delays for each command. The integration report mention before is where you get the ID’s for the light that you want to control that you enter into that command so SC knows which light to access.
Simple Control has more info in this subject on how to do this on their site. https://www.simplecontrol.com/knowledgebase/lutron-caseta-smart-bridge-pro-control/
I found after talking to Will if I create an activity and enter my lighting commands (for example when I want to power on to watch tv or any sources) into this activity I then can hide this activity from the dashboard so it doesn’t show up but I now have a quick way to add this to all my ‘Watch ?” activities as a command to execute this hidden light activity, Instead of putting in each command manually over and over for each activity.
Now that I have went thru this process it pretty straight forward and works well.