I like to start an Applications -> Utilities -> Terminal session, and then run the following command:
sar -g 60 100
which will report the number of pageouts every minute for 100 minutes (adjust the values to suit your tastes).
Now use your Mac as you normally would. Come back later and review the pageout values in your Terminal session.
If you have mostly zeros, or an occasional blip that you never noticed while actually using the system, you have sufficient RAM for your usage.
If you have sustained pageout activity, especially if you have high values, then you should either stop running so many concurrent apps, or get more RAM.
If you see short bursts of pageout activity every time you switch apps, then you are between the "good enough" zone, and the "it is annoying that switching apps is so slow" zone. You may want to consider more RAM, or live with it.
If you see this behavior with your current Mac OS X version, then most likely you will see it when you upgrade. However, if you do not see serious pageout activity now, that does not mean it will stay the same when you do upgrade, so you should be prepared to monitor your pageout activity again after the upgrade and you have settled into normal usage pattern.