I think there are deals to be found in the used market, but they are far and few between when it comes to power sports. Every now and then you can find that one-off deal with someone who bought it, put less than 100 miles on it and has buyers regret, or can't afford the payments, or life happened and things changed their circumstances. If you happen to find one that has literally been no other places then someones yard and it looks that way, lucky you! That's not normally the case though. Here's a few things I keep in mind when shopping and considering used power sports equipment...
A) Many people by these things to abuse them. It's just the name of the game for some folks. They pick up the new machine, ignore or never read the break-in procedures and proceed to ride the living hell out of it...whether that's from just being naive or ignorant (no offense to those folks), if they abuse the machine, often times the harm may not be seen until a later date and roll on to the new owner.
B) Sooooo many people ignore maintenance schedules. (Disclosure, I'm an aircraft mechanic so I put an extremely high value on the importance of routine and preventive maintenance schedules. So, this may sound knit-picky). Many owners go off the idea of, "if it's not broke, it doesn't need to be fixed" and that ideology doesn't mix with maintenance. For example, "My valves are ticking, so they must be fine". The truth is, none of us will be able to hear the difference between the .09-.12" recommended exhaust valve clearance and .15" or even .06" if your valves tightened up or got loose. What that leads to is a shorter period of the valves being open, less exhaust scavenging, excessive valve wear, and carbon build up. You won't "feel" that difference now, or in another 10/20/30hrs because it's going to gradually change. But in the long term, it will make a difference. Another example is constantly exposing the machine to water and not re-greasing bearings. They're sealed bearings...but they're not "that sealed". These are just a few examples...
C) General abuse...check out the Honda Pioneer 1000 riders group on Facebook. I can't get over how many people hydrolock their engines, drown the machines, beat the living hell out of them. What's surprising is how many folks hydrolock the engines, drain them and get them running again...and think that's ok because "it's Honda tough"....not understanding the affects of water introduction into an engine running at 2-5000 RPMs. Water doesn't compress like air/fuel mixtures and it will cause something to bend/break/wear....again. Just because the engine starts back up, doesn't mean that harm wasn't done. A second hand owner may not know that this happened until it's too late.
D). Lack of mechanical knowledge. I read a post the other day where a guy stripped out some of the frame bolts and his "fix" was to cover the threads in steel epoxy putty and reinstall all of them. WTF. Again...most sellers won't report this type of stuff because if they felt it was a good "fix", they won't see the issue with it....until you have to remove the bolts.
Again, I'm probably a bit more picky than others but those are things I look at, and things I see that I take into consideration when looking at used equipment. When I was younger and new machine were simply out of reach for me financially, I purchased a lot of used machines. Sometimes I lucked out...but there are many times that I did not. Some of those machines cost me a lot of money and heartache because the the sellers weren't honest. Just my two cents.