I never ever had a failure while updating Reaper, but I am a hobby player. If it is your income, I would advise you to not change while in a project. Only if you would absolutely need a feature of the new version. But then I would make a portable version of your current version so that I always could go back to the last working version to finish your project.
But Reaper is a pretty stable program with a pretty good test team.
And always do as said above: backup your projects an settings!
BTW: you can use multiple versions of Reaper next to each other. So you could always keep your old version alive while installing a new version. You only have to export and import your personal settings.
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