Its a little bit of RNG and a little bit of micro-decision making. It's definitely hard at the start but that was a conscious design decision as the main feedback loop is short and I wanted to get the most out of the few minutes that most players would be playing.
There are also little tricks to speed things up such as standing on the customers side of the counter so you don't have to run around, trying to get a close shelf return between one customer leaving the counter and another one joining rather than waiting for them to place theirs etc.
You can also swap a non-rewound from your inventory with a rewound one in the VCR if you weren't aware? I was in two minds on whether to tell people this from the start or make it one of those 'A-HA!' moments but I may have made the wrong choice if people get frustrated before discovering it.