Only premium one word .ios have value at this point in time. Same goes for 3L.
Call.io just sold on auction for about $10k I believe, and that was by resellers most likely.
However, there's a big difference between short, strong one word names and superlatives or two words.
My point is, your names have no notablr value today, but if the trend continues, they will, as well as "sh*tty" 3ls which have no value today.
Maybe coolest can be sold but only maybe.
These are hard sells. Like Lord said, you really need premium single words that make sense in the .io extension. cool.io would be amazing. tech.io, life.io, both amazing. But when you start putting two words together or using different tenses of words, the value drops off significantly.
I'm not saying you can't sell them, its just that demand might be weak if non-existent.