Well I think there are several issues that create a perfect storm of hesitancy.
1) I'm never sure how much spin is on the ball. Generally I expect a good push to have decent backspin, but if its lighter than I expect, my loop will go long.
2) I'm not sure if the ball is going to come long enough to loop. I'm afraid of hitting my hand on the table if I misjudge the distance, so it seems safer to just push.
3) I'm conscious that the math isn't in my favor, so being safer is often times better.
Answer to #1: You will never be sure until you do it enough times that you start learning to see read and see the spin on the ball. There are ways to tell. As you practice and keep trying to do this, you start seeing more. By not trying, you are holding yourself back from acquiring new skillz. By trying and failing, you actually make it possible to get better faster even if the short term results are not great.
Answer to #2: Pretty much the same as answer to number 1 but with a few different details: By trying you get better at reading the length. There are techniques to looping handbreaker (half long) balls that get you to make the plane of your stroke low trajectory to pass forward and just over the table so that, even if the ball ends up short you still can loop it while it is over the end of the table near the edge. So, again the key is practice. Perhaps practice with someone who knows how to do these skills so they can help you if you need information you are missing.
Answer to #3: it depends on what math you are doing. Perhaps the people you are playing don't punish you when you push back a long push. But anyone who is at a decent level, can crush those pushes you showed from the game footage you recently posted. Against a player who is even half decent, those pushes would get blasted back just the way Brs described above. So, perhaps the numbers are on your side for not taking the risk and pushing against the people you are playing now. But as you play people who have those skills and are using them against you, you will find that pushing a long backspin ball that has little spin which causes you to push high and long, with little of your own spin, will end the point more quickly than trying to loop because, at least the loop has the potential to keep you in the point.
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My guess is, if you are playing 2000 level players who are not crushing those long, loose pushes, they are being nice to you. Because, even the most eccentric, defensive, 2000 level players I know, they can smack those kinds of pushes into next week if they feel like it.
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But, regardless of this, if you want to win the current game against a player who is not going to punish you for pushing those long, weak pushes, then you don't really understand what will help your level increase. If you want to improve your skills and get better at the game, those are skills you probably should be working on; and working on them any time you play someone who won't punish you for pushing long.
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And there is no reason to think of a game where you know, if you push, your opponent will push back, as a game you must win. It would be better for you to think of those kinds of games as opportunities to practice skills and improve on things you don't do as well.
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Therefore, when you play the guy in that video you recently posted, you should be practicing attacking every backspin ball that comes to your side regardless of whether it is to your FH or BH. You also should be able to footwork yourself into position to take a FH loop on a long push to your BH side. Steparound footwork is a skill that can be developed.