fwiw I don't have a horse in this race at all as someone who hasn't entered in 8+ years and someone could win 6 years straight and I wouldn't notice or care. I'm just answering the "I never understood this mindset" part which I'm assuming to be in good faith.
Creating a festival entry takes most people time, energy, and effort, in a gamble that may or may not actually result in any gain. Whether or not the payoff is "worth it" is up to that individual user, but the more cons that get stacked up (of which "will I even win?" is a big one), the more likely it is that they won't bother entering. I'm not making any judgment here on whether it's right or wrong to have repeat entries, but I think it's fairly understandable that if someone looks at past winners and goes, "Hmm, these people have won a lot, my odds seem lower than theirs," it could easily contribute to tipping the scales against entering.
The same thing can happen with seeing amazing skins that have been already been submitted as well, for the record, not just repeat entries. If there's 16 slots, but the first 3 pages have 8 entries that feel like a shoe-in to that users, that leaves only 8 slots for them to fight over with other users, and can again pose the question of "is this really worth spending my time on entering?"
Whether that's worth it or not is up to the user in question, and their motivations. Financially, it's almost never going to be worth it compared to doing other, more lucrative activities in the amount of time spent, so you also have take that into consideration too.
Basically, tl;dr, there's a lot of factors, and the more negatives you stack up, the less the positives make it feel "worth" doing.
Re: Fest skin wank again
Creating a festival entry takes most people time, energy, and effort, in a gamble that may or may not actually result in any gain. Whether or not the payoff is "worth it" is up to that individual user, but the more cons that get stacked up (of which "will I even win?" is a big one), the more likely it is that they won't bother entering. I'm not making any judgment here on whether it's right or wrong to have repeat entries, but I think it's fairly understandable that if someone looks at past winners and goes, "Hmm, these people have won a lot, my odds seem lower than theirs," it could easily contribute to tipping the scales against entering.
The same thing can happen with seeing amazing skins that have been already been submitted as well, for the record, not just repeat entries. If there's 16 slots, but the first 3 pages have 8 entries that feel like a shoe-in to that users, that leaves only 8 slots for them to fight over with other users, and can again pose the question of "is this really worth spending my time on entering?"
Whether that's worth it or not is up to the user in question, and their motivations. Financially, it's almost never going to be worth it compared to doing other, more lucrative activities in the amount of time spent, so you also have take that into consideration too.
Basically, tl;dr, there's a lot of factors, and the more negatives you stack up, the less the positives make it feel "worth" doing.