As a LIDO user, I hate it. Most of our staff despise it too. Why?
Well, a lot of the promiesed functionality has yet to arrive. The TAF/METAR/NOTAM reader is unreliable. IE, just now I was told an alternate was not needed for an arrival airport.. Lido didn't read the tempo. A lot of this comes from the actual coding of the wx/notams by what ever state issues the info. But a lot of times, it just doesn't get it. The suitability check is not useful to me. The probelm you mentioned with the wind switch has caused several issues with our carrier, and resulting new procedures and the occasional LOI.
I think the biggest heartache I have was the functionality we were promised, and based our workloads off of, hasn't been delivered and thus we're getting hammered. WHen we relied on the planned functionality, we got bit so to speak... and now we don't trust it. A bit like having your woman cheat on you, she says never again but... So, after some certificate action... we're told to pretty much ignore the suitability check and don't rely on the alerting function. Then there's the weekly outage we seem to have every Monday morming to install patches. Often the 15 minute outage can extend for a couple hours, though that's becoming less and less of an issue when the delays starting piling on.
And there's some buggy code, for instance we have issues with redispatch calculations being inaccurate and thusly we have banned redispatches. May favorite though is running scenarios for MFT, MTT, and MCT and having the MFT be quicker than the MTT, but the MTT costs less than the MCT. Happens a good bit crossing the oceans. There the over optimization issue, where the altitude porfile can look like a roller coaster track (and through terrain... seriously), and in the US it's hard to plan point to point across the country due to lack of waypoint connections in the database.
other than that, it's great!
The only only other system I've used is NavTech, which by no means was everything for everything. But I never had near the issues with support and outages.