At the risk of sounding totally boring......
Wife and toddler = comfort reliability and convenience. Comfort = not too hot or noisy. Reliability = modern, for the most part. Convenience = four doors to mount a child's seat in the back and provide easy in/out of said child, and room to carry lots of kid stuff and folding chairs and icebox in the boot. Happy wife, happy life. Wife is not happy if 60s cruiser dies on the side of the road--at night, in a storm, in a heatwave, on the way to a car gathering (that she wasn't too fussed on going to anyway but has come along to keep you happy) or a long way from home.
That said, Lyn and I used to put Craig and his sister into the back of the Healey and head off on interstate rallies -- wing and a prayer stuff!
So my choice for a modern -- Audi RS3 sportback.
https://www.carsguide.com.au/car-rev...uy-video-40234
or for a cruiser, 65 Chevy Nova II that has been really well resto-modded with LS1 or 3 and bullet-proof electrics and cooling systems, and of course, aircon.