Not complicated, but it will take at least for you to stay an overnight somewhere in Singapore, at a hotel or somewhere that will accept 5.
Either a connecting room, or a 2 bedroom serviced apartment.
No way can you make it to Johor Bahru train station.
Getting a taxi from (larger taxi) from Changi to the bus station will take some time, and then the SBS Bus #170, either from the city centre or from one of the MRT stations to Larkin, will also take some time, and then from Larkin getting to the JB railway station will also take time.
While Singapore is efficient, once you get across the border, things work at their own pace, so to speak.
If you give it an overnight stay in Singapore, you don't have to rush. But if you try to get across to JB railway station by 9pm, I say you will not make it.
For a party of 5, going aorund by taxi is better, esp from Changi to city/that MRT station where the #170 goes from to Larkin.
A taxi might, MIGHT being the operative word, might be able to take you all the way to JB railway station, but that is a grey area, I have not done it, (but have been to Singapore) many times. Some pages on google say yes, the Singapore taxi can take you all the way, but $$$, others say no.
Best solution: book a larger hotel room or an interconnecting room hotel in Singapore, enjoy Singapore for that one night, then go up about lunch time or early morning, say 11am that day to make it across the border.
Judge for yourself.
To sum up, I say you will not be able to make it that same night.