When Maine refers to "2%'ers" I think he is referring to those rare boats out there that are pristine - in new or better than new condition.
In those case, a "bargain" price would be better compared to a new boat price rather than the used market range for the same or similar boats.
If you use that perspective it's easy to see a relatively expensive boat as a bargain. Buying what amounts to a new boat for say 60% of the new price compared to paying say 30% of new for a typical, well used boat that requires a significant investment for the "usual" upgrades can be an astute purchase.
I've sold every boat I've owned--they were in good shape when I bought them and I owned each for about 8 years--for MORE than I paid. The reasons:
* Models that were in-demand due to solid construction and good design.
* Maintained in good condition. This included minor refitting as needed, not simply replacement of what broke. Engines, rigging--what ever was needed to keep them in good condition. My notion of "good condition" is relatively strict. In one case I rebuilt the trailer (axles, bearings, wheels, tires and lighting) even though one broker though this was silly and was not interested in listing a "specialty boat." I sold her in 3 weeks without a broker (several offers); the purchaser flew up to see her, put her on the trailer and dragged her 1500 miles behind a rental car.
* Some additional refit/paint as needed just before sale. There is no point in leaving relatively simple things for the next guy, if you can do them for less than he fears they will cost. If you know your boat, you should, in theory at least, no how to maintain her better than the next guy. Make it look like you care.
I'm comfortable that none of my buyers had problems in the near term.
As Mainsail said, "condition, condition, condition" + in-demand design.