If I find that an answer with less upvotes is more helpful, is it better to side with the community by accepting the highest upvoted one or not ?
For context, my question about the morning alarm when sharing a room. The widely accepted answer is the one about the electric shock wrist band, but I personally found the vibrating phone alarm/wrist band more helpful as it's more affordable and less abrupt than an electric shock.
Yes, this is not an issue (afaik) and this happens with a lot of questions on this site. To quote the relevant page on the Help Centre:
It [Accepting an answer] simply means that the author received an answer that worked for him or her personally,
So the tick only means that the answer works for you and not that it is the most popular answer. (That's what the votes are already for)
Deciding which answer should be accepted is entirely up to the asker. Historically, it's been treated as roughly analogous to "this is the answer that helped the OP the most." You're welcome to choose the highest-voted answer, but you should never feel like you have to... nor do you have to choose an accepted answer at all, if you don't feel like any of the answers were helpful enough to you, personally.
To add to drat's answer, you can take a look at the populist badge.
It says
"Highest scoring answer that outscored an accepted answer
with score of more than 10 by more than 2x.
This badge can be awarded multiple times.
Stack Exchange badges (they say) are intended to reinforce actions which they consider to be desirable. So SE officially encourages this behavior.
ie It may or may not be the most prefered options but it is explicitly an approved one.
