I understand your point.
I just listened to the ATC tapes (liveATC) and learned of the following:
For those that knew them, the pilot that was working the radio had a slight accent (Latin?, not sure).
Pilot could not accept LINDZ departure procedure because they could not climb to 16,000. Instead they would depart VFR. Ground asks what their intentions were after departure, if they were going to go “‘down valley’ before east bound turn or going to go ‘northeast though the ridge?”. Pilot responds they would make their decision once they took off, “once we see what’s going on”. Pilot stated several times after takeoff that he wasn’t familiar with the area and asked for clarification on the valley ATC previously mentioned.
It sounds as if the holding pattern climb was either last minute decision or was an option that they took advantage of, rather than being a definite plan before takeoff to climb in that holding pattern. Tower said to climb while over the city of Aspen.
Pilot was advised to notify tower when they reached a suitable altitude for continuing to the east. They eventually said “we are going to continue east, we are above it”. Remember this was when N36JJ was at about 10,000 feet. Tower acknowledged and then a few minutes later advised them frequency change was approved because they were leaving his airspace. He immediately responds and asks what frequency was recommended but Aspen didn’t hear that and acknowledge, because a few minutes later tower again says frequency change approved. The airplane didn’t answer. They either tried their own frequency, we’re out of range, or worse. Aspen tower never said anymore to them and didn’t call them again.
Yes, they were totally unprepared.