I read through the comments so I believe you understand about tagging up and advancing after the catch. To put it simply, if they are not fairly certain that the ball will fill in for a hit, they will go back to their base and tag up. Then it is a judgement call by the player or coach whether they would succeed in advancing a base after
The catch. This depends of course on things like how fast the runner is, where the ball was hit and the angle/position of the fielder, the arm strength/accuracy of the the fielder, how many outs there are etc. Some runners are so fast they almost always easily advance. Some fielders have such strong and accurate arms that few attempt to advance.
A runner on second will almost always advance to third on a deep fly to right field. Unless the RF has a cannon and the runner is slow as hell.
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