What are some things I should take into consideration when thinking of getting a car?

I've been a car owner for about 5 years now. Bought when COE wasn't too crazy, and I have been thinking about whether to consider getting a new car since my car is approaching 5 years old and the free servicing is running out.

Back then I didn't think too much about it because I assumed this car that cost me around $85k would last me till the end of COE for around 7.5k/year if I minus the scrap cost. But looking at the COE prices now, I wonder what would be the best way around looking for a new car, or whether it's worth looking at all, considering that an average model car would cost around $150k before discounts and trade in, and thus cost around $13.5k/year at least.

Are there better workarounds such as targeting a particular year used car at certain depreciation instead? Or prob just hang on to my current car and consider renewing COE even?

Just wanted to seek some thoughts since I don't really have friends in this line of work. Thanks!

Edit: forgot to add that I do have a kid, and on weeknights and weekends I ferry my wife around for her work (sales)