That's why you don't buy new. You never buy new. A quick search of AutoTempest, and I can find several Siennas and Odysseys between $15-$25k. I found a 2015 Sienna Limited within a 30 minute drive of me for $20,950. 91,000 miles. It's got leather upholstery and a sunroof. It's got second row captains' chairs, automatic headlights, and phone connectivity (probably not car play but a so equipped aftermarket head unit is maybe 500-1,000 bucks). And Toyotas are great cars. 91,000 miles ain't nothing. All I'd be concerned with is when it last had a timing belt and water pump. That should really be all it needs. If it hasn't been done, I bet you could tell them you'll pay asking price if they throw that in.

And if you've got the extra money and want something newer, why would you pay $39k for a new base model when you can get a 3 year old Platinum for $44k? Because I found one. Has the tech in cars between 2021 and 2024 changed just that much?

As for being fashionable, that costs money. Being cool costs money. That's why trucks cost $100,000 these days. If price is your top concern, you'll save money buying a used minivan. And you can haul all your coworkers to lunch comfortably too because minivans have third rows that are meant to be used often.