Honda Pilot vs Toyota Highlander. Which should I buy and why?
I would go Highlander. In my opinion, those are better built than even the Honda Pilots which are already solid vehicles. Plus I like the design better, but that is subjective.
Are you looking at new or pre owned?
New all the way.
Depends! If you really like the Pilot better than get that they are both excellent some like the Highlander better some like the Pilot. Personal preference. Its new neither should have problems for a long time. How long do you think of owning it? 10 15 years? Then both would do the trick. If your going for like 30 years then even the newer Toyota's might have issues but the Highlander may have a better transmission in a time like that. Personally, forget about the reliability difference as they are both good and focus on what is iportant to you, for example performance, efficiency, style, size, etc.
The new generation of the CR-V is much better than the Rav4 in lot's of ways I mean the newer rav4's are extremly cheaply made compared to the other ones. The Highlander is a much better made vehicle. Honda makes the best engines I have not been in a Pilot but they should perform pretty well and be extra reliable.
I would probably keep the vehicle for at least 10 years maybe longer.
Get the Highlander, it will outlast the Honda Pilot. The automatic transmission on Honda Pilot is not comparable to Toyota.