To be quite honest, and as usual, quite frank, and in no way trying to offend you, but this must be about the most stupid question I have seen in a long time.
This is not a seasonal fruit, so there is no good or bad time. This is not an investment, where you can expect a certain return, so it should not be considered a such.
This is something that you say you would like, so it would be a case of, yes I have the money, or no I don't. And what the hell has Parker's valuations got to do with it? They most likely have a couple of prices, and then a standard way of deriving other prices for cars in different conditions.
That might work if they are selling VW in the thousands, but surely it has little meaning because there are only normally a few V8s on the market at the time.
So step out in the wide world, and make a ****** decision, if you can and want, buy one and enjoy, if you can't or won't, don't and don't.
I have just lost a friend, wrote himself and his Healey 100/4 off. Life is sometimes just too short.
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