For Highland, I'd go for an Aberfeldy 12 and for Islay, a Bunnahabhain 12, both are very approachable drams for around 40 bucks a bottle. The Aberfeldy is unremarkable next to the Blair Athols and Glen Gariochs of the Highland world, but an amazing value at the price point. The Bunnahabhain is one of my favorite Islay pours, it cheaper than its neighbors, and a more approachable starting point for someone who isn't that familiar with the smoky ways of Islay. If he loves the peat smoke then Laph10 by all means, but for some who are just starting out the Ardbeg, Laphroaig, Lagavulin trio might be a bit much.