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4. Possibly at end of life to clear stocks (PS went on sale at the end)
So the best way to minimise the risk of missing out would be the start with the oldest and work forward. But be prepared for the Parisian Restaurant to be retired next before Palace Cinema, for example.
I never followed this advice though and have bought 5 modulars to date. In order, these were Palace Cinema, Detectives Office, Parisian Restaurant, Pet Shop and Brick Bank.
I got the Pet Shop within days after it's retirement was announced (well persuaded my wife it would be the perfect Christmas present for me).
As far as the order of them retiring, as was mentioned it's not always oldest first. I believe it was the Town Hall in 2012 that retired before the Pet Shop from 2011. Granted that is the first time it happened to my knowledge but something to keep in mind.
I tend to try and get the oldest one first. That being said if you are only able to get one within a long period of time I would wait for the announcement for one to be retired and then purchase that one. From there go back to the First in first out thought process. with most of us now it is just figuring out what is the best time to buy the new one.
Buy them all if you can afford to, wait for the 2X VIP points to get a better deal, since they don't usually (if at all) go on sale. The only one that has gone on sale, like mentioned already, has been Pet Shop, but I am sure they did so to get rid of stock (not as popular as others).
The only go on sale if LEGO is trying to clear out stocks, or if LEGO did clear out their stock which seems to give other retailers the ability to then put their stocks on sale.
For comparison, the new USC snow speeder (#75144) is 1703 pieces for $200.00 or 11.7 cents per piece. Double the price!
My point? Don't risk missing out on currently available sets chasing a sale that probably wont happen. They do not get cheaper after retirement despite how many everybody has stashed.