I am afraid it is very easy to get confused with dynamic pricing - in fact I would go as far as to say that it is almost impossible NOT to be confused!
Whilst I accept there are winners and losers with this system, with the main losers seeming to be those looking to book holiday flights during school holidays, I think it is an awful development.
Anyone who is planning a trip involving flights or upgrades, and are paying for their own seat(s) needs to know how much they are going to be charged, so that they can factor this into their budgeting.
You came here asking for advice, but I really don't think anyone (including VS staff) can give to any - it seems every time anyone tries to book / upgrade, they get different prices.
I realise that this is the whole ethos of dynamic pricing, but it doesn't mean I have to like it!
I think it will drive more and more people away from points collecting and from VS!
Nick