I'll be honest, I have my own misconceptions about YC and it's put me at an impasse of wanting to apply.
1.) From what you read, it seems like everyone has a positive experience. At least in my network, that doesn't seem to be true. I'm not applying the logic that it sucked for X, therefore it must suck for everyone. I just want to know who YC works best for and who it doesn't. After all, the old adage goes, if you're selling to everyone, you're selling to no one.
2.) Following up on that point, I thought very few enterprise startups did YC and that YC would be weak in that category. From the stats, it seems like a majority of startups were enterprise focused! But, the standard YC terms kinda suck for enterprise startups. If your ACV is +$100k, why raise $120k for 7%?
3.) When is the right time to apply? Taking some thinking from pg, you should make 100% focus your customers and product. If I needed to raise $ now and wasn't accepted into YC, I would just go try raise money at that moment. Seems odd to hold out and keep trying.
Once again, I think most of my points are misunderstandings about how YC works. I don't think this should help reflect anyone else's decision to apply. I think it's very likely that I will apply to YC. I just wanted to get some of my thoughts out.