Hi James_Franklin,
welcome to the community. Hope that you enjoy live.
Unfortunately your uploaded screenshots are not shown, make sure that you do it on the correct way next time.
Requesting Takeoff must be before you enter the runway. How to hold short correctly is explained in the post below:
Only if you are cleared to line up OR for takeoff you are allowed to enter the runway. By the way: The Training Server 1 (TS1) should be the right one for you.
For takeoff you should only use the runway, can not see your screenshot but a taxiway is for taxiing ans not for departure.
And no, your questions are not stupid. Everyone began new and didn’t knew everything correctly.
Happy Landing and met me know if I could answer your questions a bit.