I have not sailed a Highlander, but I have heard good things. Do you want to race? If so, look into which boats have competItive fleets nearby. On our Lake it’s a no-brainer, the Scot and Thistle fleets are the biggest. Lots of good competition, and advice, and a ready resale market for these boats.If you routinely sale with one crew, the Scot tends to be easier for this. Competitive Highlanders, Thistles and lightnings, are often three-up.Age, fitness and comfort level also matter. The Scot is the easiest to sail until you are truly ancient. The Thistle requires a little more athletic style, and is physically more demanding.On the lightning or highlander, if they are the strongest fleet where you sail, they would be worthy of consideration. For the Highlander it seems the Ohio area is the main concentration of fleets.One other aspect of the Scot is that it is really easy to find a competitive boat. All the boats are fiberglass, and most are Douglass or FS Inc built. As such the difference between boat ages, builder, and condition is somewhat narrower.Where are you located?