The question might seem easy on the surface but does require a lot of thought.
This will involve family so room for passengers and the kid, let’s assume reliability, room for luggage, enough power to keep you entertained etc.
To me an E39 M5 wagon is the perfect combination of features, fun to drive and usability. Plus one of the last generations where you can actually feasibly repair everything by yourself in the long term before they got over run by over engineering.
Call me crazy and I’m not a VW fanboi by ANY means but a Jetta Sportwagen TDI would be a great all around vehicle, good MPG’s plenty of room for family, reliable motor that will last a LONG time and roof rack for whatever I may need it for.
extended cab deuce and a half M35A2. room for kids, can pull a loaded semi trailer, 6 wheel drive, carrying capacity of 7 fucking tons. gas mileage in the single digits. will run on any combustible liquid. used motor or veggie oil, kerosene, obviously gas and diesel. and it’s fucking titanic.