It's difficult to measure these things, "100 people out of several 100,000's didn't agree" is not much of an argument, but what im sure is, if segwit wasn't done as a soft fork, and it activated, there would be people mining the original chain, and we would have a 2-coin situation.
Maybe, but not necessarily. This would still have required a dev team to continue maintaining the legacy chain (ie. non-SegWit, non-blocksize-increase), especially since 2-way replay protection would still be a requirement for both chains to survive on the open market -- otherwise one chain would get cannibalized by the other rather sooner than later, as exchanges wouldn't be able to reliably support both chains. Either way such a scenario would have likely meant that neither chain would have implemented replay protection, leading to a blockchain fight to the death.
Also, it's not so much the amount of people, but the skin in the game, namely, people owning a ton of coins ready to dump their share on your chain, crashing the price, and thus forcing miners to mine back on the legacy chain.
The amount of people for the most part directly translates to skin in the game though, doesn't it? Dumping your coins on the chain you disagree with only moves power from you to people that actually believe in said chain. It follows that in the long run its more a question of fiat flowing in, rather than coins being dumped.
whats even more needed for bitcoin is to be more intuitive and easy to use in real life scenarios.
Fully agreed. But first Bitcoin needs to get its scaling problem in order, otherwise all would be for nil. Great user experience accounts for nothing if the underlying fundamentals are not ready.