I LOVE iwara, there's no doubt about that. Sadly, the site seems always stuck in a limbo state of constant errors, lack of detailed tagging system, connection issues and many more, which has impacted severely user experience, even for experienced users. This is from my subjective view, so there may be some disagreement along with the post. Feel free to discuss, and I am open to receiving corrections from other users. I am not good at making long lectures in English, as it is not my first language, but I will try my best to describe my ideas:
1. A GUI overhaul, and I'm dead serious because, by today's standard, this is extremely crucial for iwara survival for the next decade or two. People say "If it ain't broke, don't fix it.", but taking from a new user perspective, if it was not for free but quality content produced daily, I'm better off for other sites, even if I have to pay a small amount. GUI is usable but primitive and confusing.
2. Server problem. This is also a crucial point, as it has been a running problem for the last 5-6 years already. On a good day, iwara worked as expected, but sadly only on rare occasions. The majority of the time, it suffered from slow loading to connection problems, and as the time I'm writing this, downloading some videos is not even plausible due to network issues. I'm running a 120Mbps (according to fast.com) cable connection (you see where I'm heading from this). The network issue is not from my end, it is the server that needs much-needed attention.
3. Tagging function is broken. I believe everyone who has used this site for over a week will agree. Given how barebone and severely limited the tagging function is, no wonder why people have screamed for years. Also, there are cases that people tagged the wrong tag, giving confusion to other people. Remember when Genshin Impact tag does not exist yet? People blatantly tagged the wrong tag to those videos (and you can still see the aftermath today by checking Touhou Project tag).
4. Search function is disappointing. I wish I can specifically search videos or images only. Also, the lack of a thumbnail for video posts in search makes me have to play a guessing game whenever one's suitable for my need. It is just disappointing that I have to waste my time just to find the right video. Finally, private posts in search results are just frustrating to look at.
5. Private is abused too much. Private function is meant to protect your hard work and effort from being stolen or re-distributed to somewhere else, and I highly respect those people who used it correctly. But some people just like being an arse, locking their collection outside public view and NOT accepting friend requests.