The best way to check if you need more memory is to close everything and restart your computer in the morning. Then do your normal work that you do every day. At the end of the day open terminal and type in vm_stat and look at the Pageouts number. If it is significant, then you would definitely benefit from more memory. In my case it is not and that is over two days clearly.
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Having said that nearly all people would benefit from the 8 to 16 jump. Modern operating systems will use as much memory as they can to cache frequently accessed files. This makes the OS experience feel more snappy and responsive.
Do I really need 32 GBs of RAM in this machine? Clearly yes, because even though I have not done anything intensive in the last few days, my cache is huge. It makes multi-tasking and having multiple applications and windows open a much more seamless experience. Would I benefit from more though, like 64 GBs? Probably not. As with everything there is a cost vs performance tradeoff that is first steep and then levels out.
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