taking the hit early while the sled is still new enough that lots of people want it for a couple grand less seems to be the most logical, if you can afford it in the first place. It also really depends on where you're located. There are lots of mountain sleds for sale privately around here in ND and MN for to high of prices. People don't like giving their money away with a 1 or 2 year old machine, but if you look at sleds for sale in mountain states on the classifieds, much better deals to be had. I wouldn't say there are a ton less mtn. sleds available around here, the market is just different. It costs a lot more to get them to the hill for us. I let my last pro go for a little less than I thought it was worth, but when there are so many options, the next guy is just as hopeful to make a deal as I was.
New sled prices are awfully high, but as I said before, you won't be paying that sticker price, and if you are close to those figures, you're getting lots of warranty or accessories or both. Holdover spring prices are always the best of deals when it comes to new machines. Someone with 100-300 miles on their sled considers it new still, and usually isn't going to come down on price much. Been there, done that. Its tough when you have a new toy in the shop and you're not getting to use it like you thought you would. Makes it tougher to give it away at a bargain.
I think there are all sorts of great machines out there to choose from. I often wish I had all sorts of money to just buy up good older sleds for great prices I run across every now and then. If things got really tight for me but I could still ride some, I'd dump my '15 Pro TD for $10k with a couple add-ons and go find an '06 M7 for $3k. I'd love to have an M7 backup sled laying around, but when you only get a few hundred miles on a year and your RMK has always ran flawlessly, It's hard to justify another newer machine.