When you're aiming at consumers, I think <$5/month or <$50/yr is definitely a better price point. I think Flickr Pro's ~$25/yr pricing is much more in line with something most consumers would go for. And that's even at the semi-pro level. But, when you're aiming your app/service at professionals, freelancers, or small/medium business, then slightly higher prices might fly. Still, though, there are so many "must have" apps now, that the subscription fatigue should start hitting people bad.
What I'd really like to see is more webapp service synergy. Most of us would be much more likely to pay $10-$15/month for Dropbox + Evernote Pro + Backpackit.com Personal (substitute your favorite webapps in here) than they would to pay ~$5/month/service. Something about the bundling would make people feel like they're getting more for the price, even if the absolute price is the same.
What I'd really like to see is more webapp service synergy. Most of us would be much more likely to pay $10-$15/month for Dropbox + Evernote Pro + Backpackit.com Personal (substitute your favorite webapps in here) than they would to pay ~$5/month/service. Something about the bundling would make people feel like they're getting more for the price, even if the absolute price is the same.
At least that's my $.02...