What was the early American liquor trade like generally (e.g. relative price per unit, variety of selection, volume)? It strikes me that today we associate liquors with specific regions (Kentucky Bourbon, Carribean Rum, London Gin) would this always have been or might our hypothetical Bostonian have had access to Boston-brewed variations of the above? Would anything have been locally-brewed in Boston?
How different might my drinking preferences be from a frontiersman in Tennessee, or a Londoner?
I can't give you details about Boston, but there's a very famous liquor bill in Philadelphia from about this time: that from the party after the Constitutional Convention in Philadelphia, with prices in pound, shillings, and pence, though it's unclear if this is standard British pounds or some other currency. The dinner was in honor George Washington.
54 Bottles of Madera………………………………………. 20 5
60 of Claret ditto…………………………………………… 21
8 ditto of Old Stock………………………………………… 3 6 8
22 Bottles of Porter ditto…………………………………. 2 15
8 of Cyder ditto…………………………………………….. 16
12 ditto Beer………………………………………………… 12
7 Large Bowels of Punch…………………………………. 4 4
Madeira is a fortified Portuguese wine, like Port. Claret is a type of red wine from France. Old Stock here is a type of whiskey. The others should be self explanatory though it's of course very unclear the size of these bottles. Punch in these days was alcoholic punch, and from the recipes I've seen rum is the most common alcoholic ingredient, but brandy is almost as frequent and I believe I've seen whiskey and gin containing recipes as well. Here's an example of one that claims to be a 18th century recipe with "Jaimacan rum", "Remy VSOP" (cognac/brandy), and "Mathilde Liqueur Pêche" (peach brandy).
These are rather elite drinks, of course, most of them being imported. I've read that both whiskey and rum were the most popular distilled beverage in this period (and perhaps it changed in this period as West Indies Rum became more expensive). It's worth remembering that one of the most famous early rebellions was the Whiskey Rebellion in 1791-1794, which occurred in Western Pennsylvania against an attempt to federally tax domestically produced distilled spirits (not just whiskey, but the fact that it was called "the whiskey rebellion" should say something about whiskey's popularity). It was as far as I know the first federal tax on domestically produced items (most prior taxes had been custom taxes), though I'm far from an expert here. Considering that most of these distilled alcohol were made in local stills, I'd imagine in Boston you could find locally produced whiskey and rum, though I'd guess you could also find whiskey produced elsewhere and brought to Boston and of course Caribbean rum and perhaps "Batavia Arrack", a type of rum made in the Dutch East Indies.
I'd imagine you'd also be able to find various lagers, ales, and porters, I assume mostly locally brewed though I don't actually know. The Adams family (including Samuel Adams) owned a malt house for malting barley, so clearly a good deal of it was locally produced. Cider was also an important local beverage--Johnny Appleseed's legacy involved planting apple nurseries in Western Pennsylvania, Ohio, and Indiana. These were not beautiful eating apples (those require cloning and grafting; all Red Delicious apples are cloned from an original tree, for example) but rather what are sometimes called "crab apples", which are meant primarily for (hard) cider making. "Applejack" was an easy to make strong beverage--it involved "freeze distilling" hard cider. Basically, one would leave cider in out in in the winter and some of the water would freeze. Once this ice was removed, you'd be left with a more highly alcoholic drink.
So, I managed to give you a lot of information, but no clear answer to your question about what would be "typical", only some sense of the range of products available.
If I can add on an additional question: I was taught in school that New England served as a step in the triangular slave trade in the Atlantic, turning Caribbean sugar and molasses into rum. Is this accurate? Would this have been the case for Boston in 1800?