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On the flip side, any of those machines should last a lifetime. So also worth spending a bit extra for something reliable.
I'm not that knowledgeable about how long the Flair or Robot are going to be around for, but if you think they might be relatively limited, might be worth getting some sets of gaskets for the inevitable servicing.
I've yet to need anything done with mine, but I can rely on the gaskets being available when I need them!
No experience of them but I've seen (as I'm sure you have) James Hoffman's reviews of them. They do look very nice!