Jump Complete
"At this point I was at 3000' with a ridge of high ground (a peak height a mile to the left of my track was shown at 2100') "
Now I may be getting the wrong end of a sharp stick here but if the ground is a mile to left of your track how will it impinge on your descent to 2000'? I am sure that a controller would not give you a level that was impossible to fly to enter CAS on. I think that from the reading of your post several times you may be getting the levels allocated to aircraft confused due to your flight rules.
If you are IFR the pilot is responsible for his terrain clearance ( 1000' above the highest fixed obstacle in a radius of 15 miles?) initially, and then the controller will allocate a level that is terrain safe (no pun intended!) depending on the service that is being provided.
If you are VFR then the controller will allocate a level to enter on, you do not have to descend immediately only descend so that you will enter at the specified level.
You initial post was interesting and lengthy but I feel that we are missing out on some more information.
TS