Spodman
Well said. ICAO does promote this confusion, I think, by putting a double arrow on the illustrations in 4444.
Numpo
Your f'rinstances:
1. No. At the time the first passes the VOR, you have already lost separation, although I grant you, you might be able to regain it very quickly depending on particular tracks and whether DME used.
2. No. As No 1 - even if the second aircraft has been instructed to hold, you have lost 10 min longitudinal, and you can't claim 5 min from the holding pattern because the second aircraft ain't yet in the hold -he's thundering along in the same direction and eating up the space between.
3. No - see my example. You have lost separation at 1210 unless another form of separation, usually vertical, is established by that time. At 1220, the aircraft are 1½ min from collision. In the original example posed by Yeg, the situation might not be so hazardous but the principle is the same.
The variations suggested by some correspondents might seem reasonable, might be quite safe, but are not necessarily application of provable separation minima.