It depends on what you're doing with the chocolate.
If temperature isn't that critical and its going to be mixed into a cake or brownies or such, then do it in the microwave. Its simpler and as long as you don't rush it, its does a good job. Just go 10-20 seconds at a time, in bowl that doesn't hold heat well.
If you need precise temperature controlled chocolate (for tempering perhaps), its best to use a double boiler. The bottom pan just has steaming water - so I never really count that as a dirty dish. With the double boiler, you get several advantages. It won't get any hotter than the water. It its gradual and gentle. And you can monitor and stir as the temperature rises. If it turns grainy, its likely a bit of water dripped in. Depending on the top bowl on the double boiler, its possible to accidentally knock some condensation into the chocolate...and now its toast. I use a top bowl that has a small outer lip on it to keep this from happening.
Whisk(e)y has some crazy chemistry going on inside of it, due to the complex interactions between water, alcohols, oils, esters and other compounds of various complexity. The profile of these chemicals will vary between different whiskey/whisky styles, but the overall chemistry is similar.
Simple effects of dilution
Adding water, or serving on the rocks, has a number of simple effects, such as diluting the ethanol a bit (ethanol anesthetizes your taste buds a bit), and cooling it (making your taste buds slightly less sensitive to certain flavors), but the fascinating part is what happens to the oily flavor compounds during dilution.
Dilution masks some flavor compounds
Oily hydrocarbons are somewhat soluble in high-proof whiskey. There are long-chain esters and short-chain esters of many varieties. As you add water, the whiskey becomes more polar, and the long-chain esters become supersaturated and start to precipitate in the form of micelles, microscopic "droplets" of esters that have clumped together. In some liquors like absinthe or ouzo, these droplets can get so large that they become visible, and visibly cloud the drink (an intended feature of absinthe preparation). In whiskey, these droplets are usually microscopic and don't visibly cloud the drink, because most of the oils have been removed during chill-filtration.
However, these droplets do something important, in that short-chain esters, being more soluble in the droplet than they are in the diluted whiskey, enter the droplet and become trapped inside. These compounds are now less available for tasting or smelling. Fortunately, these compounds are the oily, grassy compounds that many people do not like in their whiskey, and masking them is considered an improvement.
Dilution releases other flavor compounds
There is another type of micelle "droplet" that forms in whiskey. Ethanol, in high concentrations in water, forms it's own clusters, as ethanol molecules gather up with one another. Interestingly, warmer solutions cause more clustering of ethanol molecules, as do higher concentrations. Like before, these micelles trap compounds that are more soluble in ethanol than they are in water, volatile flavor compounds. However, unlike the oil droplets, these flavor compounds are desirable. Cooling the solution and diluting the solution both serve to "pop" these ethanol micelles, allowing them to release their trapped compounds for aroma and flavor.
So cooling and adding water can have the effect of both masking certain flavors by forcing them out of solution, and enhancing others by promoting their release back into solution. In the end, the result of the changed flavors is a matter of taste, which is why some people prefer neat, with water, or on the rocks, but one cannot deny that real chemical changes are in play.
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Best Answer
Honestly, "whatever you want" is the only answer :)
I have a similar seasonal recipe, and in various years, have tried:
The flavors of your chosen liqueur will be somewhat muted by the chocolate, and so something with the complexity of Drambuie was a bit of a waste. However, ultra-cheap bourbon was a little disappointing, as it provided booziness but not much other taste. Kahlua, Grand Marnier, and similar choices with their own flavor profiles can play very nicely with the chocolate, so it's also OK to get creative.
The best choice is a bourbon (or other) that you might enjoy sipping on its own, ideally one that is already on your shelf (if you don't mind sharing 1/2 cup of it). If you hate a particular liqueur, you won't enjoy this dessert as much! If you don't know much about whiskey or have much interest in it other than as an ingredient, a mid-range price is probably the way to go. Asking the proprietor of a liquor store can often result in a good brand recommendation.