It depends on one's expectations and planning.
Problem with most people is they like to compare. You what what they say in Chinese, "Ren bi ren, qi si ren". No matter how rich and comfortable one is, there is always someone even better. Funny thing, we humans never look at the less fortunate and say Hmmmm, we are so damn lucky despite living in expensive Singapore and small flats!
Many new uni graduates in Japan, Korea, HK and Taiwan can't even afford or dream of paying for their own apartments. They have to rent. And I'm sure all of us know how tiny a Japanese or HK home can be in the city. Our 4 room BTO flats at 80-90 sq m is a luxury to them. Personally for me, too big a home is actually worse! I can afford it but I don't need it. I don't like to keep extra things or rubbish at home. You can say I'm simple.
If one had bought a public flat in Singapore, the price appreciation of the flat can be so much higher and faster than a condo in JB. With that added monetary gain, you can then decide later if you want to retire in JB or move over.
But if you buy a property in JB or other parts of Iskandar ( especially those recently) the money could be stuck there indefinitely, unless you don't mind or have this part of the finances covered.
Also, as I've mentioned, sometimes time is not replaceable. 1-2 hours each way can be considered a lot. Some have kids. They can't be moving around like that. There's stress. Some must reach work at a certain time. No frequent delays are acceptable. Others are afraid of the lack of safety. This is valid. All these may not be worth it to sacrifice just to get a bigger home.
I must say that if one has it worked out nicely, then yes, work in SG, stay in JB. It's definitely a possible way.
I would def do that, but stay near to checkpoint in JB. I used to work in China and travel few hrs to work is the norm, just another day in the office.
I see many people having "quality" time on their phone when eating out with family, all the time. It's how you utilize the time given to you that is important. My friend in China travels almost 2hr/way to Beijing to work from Tianjin but she said that 2 hrs is "me", also she gets a lot of work done as no one bothers her. Then i visited her house and it was like WOW! Granted she is still young. She said those stay in downtown BJ may have better life for now (debatable) but she will surely retire much earlier in the long run. These China fellas are damn hardy.
Another point is, JB offers a "choice", you can have "cheap" if you sacrifice something, but in SG there is no choice, only exp. You want cheap, you have to share a HDB with 2-3 other strangers, that's not quality of life to me.