Although @spesimen is right in his reply , I believe it added more confusion to what you already have and not totally answered your questions.
1. that is correct you don't normally file a SID/STAR as part of the flight plan, although VOXAtc supports those if you do decide
to file. In general SID/STAR are based on the RWY in use and the air route which you came from.
2. as to your "complicated" question on how to set your plan to include the waypoint which in return trigger a SID/STAR?
don't sweat over it. file a flight plan from the Airport, up until the airport (usually the airport VORs), 99% of the times the SID/STAR waypoint will be in it already,
under the assumption there is a SID/STAR for that airway. VOX doesn't needs the waypoint to be at the beginning/end of the flight plan to assign you a SID/STAR.
it just needs to contain it.
99% of the flight plans you will download from all kind of FP tools and websites, such as vroute, etc., contain the SID/STAR waypoint in them already.