These are all things we are keeping in mind as our Subie's mileage creeps up, 167k+ right now. We are starting to keep a running thread of various makes/models as possibilities.
The problem with giving up things like Apple Play is that it is really expensive to get it back, because these 2010’s cars and trucks have a lot of functionality built into the OEM head unit. You are walking in the door at $750 for the head unit + Maestro Datalink and that’s if you can install it yourself. I just did on my 2008 Sequoia and that’s probably $500 at an audio shop.If I didn't have to buy new now, I would suggest not. I would be looking used and be very open to finding the best example and maybe willing to travel. Granted you might have to give up some technologies like park assist and Apple Play but you are still going to get a ton of reliablity. I woul aslo look to the brands and models that might not be as popular and in demand ie Infiniti, Nissan, Mitsubishi and even Acura. I'd also look at sites liek Cars and Bids or Bring a Trailer where there is a level of vetting of the cars/trucks listed.
As someone who made a living buying extraordinary values in old Toyotas, that is gone. My son’s girlfriend just acquired a very nice condition 2009 Rav4 for $11K with a 157,000 miles. That was a nice enough score right now, but is a horrendous value historically.
Personally, I would see where any OEM is still offering decent financing rates if that still exists and pay MSRP. We all have this idea of negotiating good deals with dealers, young kids today won’t even understand what that meant. We’re all holding our noses and walking out the door, but that’s just because we are old and stubborn now.
There is no worse value than a high priced used car.