I find I can type, say, jsmith123 into the search box and I'll somehow either get multiple users listed as having that username or a bunch of similarly named accounts, possibly ranked higher than the one I explicitly typed in.
It's really unintuitive and contrary to how people use Skype. It's using the method whatsapp, telegram, et.al use, but they don't really have a discoverability feature. You know someone, or you don't until you know someone who does.
Skype should either have just ditched the username search or embraced it. They tried to make it both, but they really didn't pull it off well, and now there is an entire subset of the userbase you cannot find with their find feature.
This last one on OSx has been particularly bad though. Its just so slow at doing even basic tasks like chatting.