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Don't you think, though, that most of Fastmail's customers are "an informed niche audience" that have already done their research and are knowingly paying a premium for Fastmail? They are not, in general, simple price-seekers and evaluate a range of criteria (including but not limited to price).
In my experience, price-seekers are a small proportion of most markets and firms cater for them (or is that 'pander to them') with introductory offers and short term discounts. That small proportion of the market tends to hop around between suppliers. But the majority of customers are inertial, or have made their purchase decision based on non-price criteria, including bad or good experiences.
I think that Fastmail's informed and most loyal customers - even those who shop around - are there because, for them, Fastmail's product is the best.
If Fastmail is seeking growth in customer numbers or revenue, the pricing scheme is a rational. Many of Fastmail's customers might be peeved because they can't readily access the new prices, but when they shop around most of them will probably still find that Fastmail's product is the best for them.
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