I bought my first new sled this last year, and had my first year with no breakdowns, downtime, or fancy extrications. That is worth a lot to me. Some guys like tinkering and fixing s**t constantly.......I don't. I work a lot and don't have the time or a big enough shop to have my sled torn apart every week. So I'd rather spend the money up front and have something that's ready to roll, and tinker with regular maintenence and the odd upgrade. That said, buying a new sled every year, or 2, or 3 is definetly expensive insurance.
As long as I don't notice the sledding cash affecting other aspects of my life I am good with it.
I bought a used twisted HCR and its the first sled I've had that didn't fail at some point (so far) even used I could dang near sell it with a warranty. When people figure out what works and what doesnt the prices will go up a little but mods are a huge looser.