Just like trying to find your favorite cigar, that's a very complicated question - one man's favorite is another's disaster...
I would start out "light" and go from there. One of the first Scotch's I came to enjoy (cased on AVB's suggestions) was the Craggenmore 12 yr - it's a Speyside Scotch that is relatively light and citrusy. Right now it's selling for about $70-80 a bottle.
On the "light" side I've come to also like the Bruichladdich Classic Laddie. It's an Islay un-peated Scotch that is just a tad bit more complex than the Craggenmore. It's a wee bit cheaper ($55-70 range) and is a great expression of a "true" Islay Scotch. I'm hooked on the Bruichladdich Dark Art, though is very costly ($500). Like it's younger brother "Classic Laddie", it's simple, elegant and complex. And it's no wonder it's over $400 more than it's younger brother - although I really don't mind drinking the Classic Laddie if I'm looking for a good dram of Scotch!
Recently I've been sampling the Trader Joe's Scotch's. They have three "double maturation" Highland Scotch's they're selling in the $17-19 range - a Sherry Cask, Rum Barrel and Bourbon Barrel finished. All three have different characteristics, but for the money they are a great Scotch that is very reasonably priced. Again - pretty "light" (unpeated) and I'm fairly certain they are Grangestone (sure taste like it to me). Given Grangestone sells for about $30 - the price of the Trader Joe's is a bargain!
If you want to venture into the more "deep" side of Scotch (generally pairs well with a cigar - I really like the Dalmore 12 yr ($60ish), but especially the Dalmore Cigar Malt Reserve. They are Highlands Scotch's that are a bit more complex in flavor. I know the Cigar Malt Reserve is a bit out of your price range ($160ish) but it beats the King Alexander in price ($300ish). I'm a HUGE fan of King Alexander.
And then there is Bruichladdich Port Charlotte - one of my absolute favorite "heavily peated" Scotch's. I love the company, their product and their link to Islay. Their story is amazing, and their total commitment to producing the best Islay Scotch's is admirable. They completely believe in hand crafting, and it shows in the Scotch's they produce. The Port Charlotte 10 yr is the most reasonable (at about $70-80), but their other Port Charlotte expressions are even better than the 10 yr. And if you can afford it - the Octomore is incredible - it is cask strength, so drinking it neat can be a bit rough - but it smooths out amazingly well with one piece of ice to "open it up".
These are my suggestions - but the journey is all yours! What I like might not be what you like. But I'd like to think I'm at least "middle of the road". Good luck and happy hunting!