In the community that I grew up in, gambling was definitely a no no if you wanted a reputation as a God fearing person who lived right. This was pre lottery, so the only legitimate way to gamble was to visit the 'bookies' and bet on horse racing and sports matches. At that time such places had a 'seedy' reputation and you wouldn't want to be seen visiting them and associating with other gamblers.
There was also the 'Pools', where you gambled on the outcome of football matches and tried to pick out a certain number that would end as score draws. My non JW dad did this every week and I often helped him to fill in the results and check how he did. I was sharing in his sin, obviously.
But the proliferation of smartphones and gambling apps has utterly transformed that aspect of betting. Now you don't need to keep 'bad company' or be seen in public having a punt.
This brings it's own dangers of course, but it's very hard to argue that a JW who uses his phone to place an occasional bet on a big football match is committing an act of sin.
Btw, that tongue in cheek emoji at the start of my post is a mistake. I can't delete it for some reason.