It seems that on most shared hosts, you find out that you need to upgrade when the company suspends your account for "resource abuse"..
However, if you have a VPS you can monitor your site's resources easily as there's usually a little panel telling you how much RAM your site is using. Once you notice that the RAM usage is getting close to the maximum amount you have in your account, you might want to upgrade the VPS or to a dedicated server if you feel that your site is growing too quickly. I'd recommend that you upgrade the VPS first though unless your budget can handle the cost of a dedicated server right away.
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