It is all about the piece of mind factor.
If you are in a position where it is IMPRACTICAL for you to be without a vehicle for costly repairs it's probably worth the payments for your piece of mind.
I try to buy rigs that are gently used and at the end of their generation. For instance, I own a 2011 Nissan frontier... because it is almost identical to the 05 model. I also owned a 2k4 Nissan frontier... because that generation was 6 years old. I like to buy rigs that have the majority of the little things corrected and if they have known items (like shotty motors and bum transmissions) I can avoid them all together.
I travel A LOT for work. I CANNOT be in a position where my vehicle is down. It is simply impractical for me to buy older, higher mileage used rigs.