I bought a 2004 in 2011 for $2800, and drove 6 hours round trip for the deal. In gas alone it was $100 more, but if you believe in your vehicle having a finite amount of miles, it was probably a $3300 ski.
I've since replaced
midshaft housing $200
throttle cable $50
steering cable $70
motor rebuilt due to a case leak, and found a worn bearing so had to do a complete rebuild $500
carbs rebuilt $150
new battery $100
new hood seal $100
$1170 more on top.
So, were at nearly $4500 for a stock setup. Next thing to be said is, "well that's still half the price of new", except a few important things...
Most of that stuff is SBT or WSM, inferior quality to what comes new. Those prices are what I paid, most of them were close to dealer prices, so about 30% less than retail. So we can probably call it closer to $5000 for retail on OEM quality parts.
Then, lets not forget that each of these items broke one at a time. A lot of instances requiring more than 15 minutes of my time, in some occasions days. Oh, and I may have owned the ski 4 years now, but most of those repairs were at the 1-2 year mark. The 1st year had a lot of down time, so did the 3rd.
And last but not least, lets not forget there are still a few lose ends. Things like my start/stop switch needing to be cleaned regularly, my paint is severely oxidized in some places, a bond rail bumper fell off, my turf is coming off, my gunnel pads are both off and need to be glued back on.
New is the right decision for many people. If I made more money and had less time, I'd be a new buyer.