I'm half and half and all very much dependent on the situation and circumstance. My hope is people will see problems for what they are and change how things are done.

The gloomy issues I see arriving are:

   Continued loss of critical thinking ...  govts. might have though a less intelligent public is easier to control, but we're slowly starting to see there is a greater cost ... it's cheaper to educate people as best can be even if they might end up with a low level job.  
   
   govts forcing adoption of new tech which is biased towards established business and no real choice for the mere user to stick with what they prefer to use -- things like forcing one particular browser or something the govt's web site developers rely on but which doesn't play well or forcing the public into endless OS update game.
   
   The moving via updating - systems that didn't have a internet interface and thus had an effective air gap, to run via web ...  and then watch the havoc when some smart arses prove how clever they are breaking though the security. 
   
   The same as above in that air gapped systems such as traffic lights / management, are moved to the web, and an A.I. is left to run the show.  The sad thing is in the future people if they don't change will just accept that some days SNAFU happens.
   
   The slow erosion of privacy by silly or over the top forms of web security, mostly to satisfy anonyphobes  ... I'm counting the months I'll need to start providing 2FA or a fully tracked browser, just to get simple information like finding out which is the better brand of bulb because that information might be abused and lead to mischief.