That’s a reasonable approach, although one thing to consider is that if you have a group of people who aren’t total food/wine geeks, then the exact pairing may not be that critical. A Moscato could be a good choice; one thing that makes the pairing a bit more challenging is having the chocolate which tends to push you in a different direction. But for a lot of guests, as long as they like the dessert and the dessert wine, it’s all good.
Paolo Saracco would completely own this category in most years [and is always the 100% reliable fallback option].
But 2012 was a such massive and powerful vintage for Germany, even at the Kabinett level. We had a 2012 Kurt Darting Riesling Kabinett down here [in miserable franchisee-protected North Carolina, with no more gray market] at $14.99 which would have been perfect for you [it tasted like an Auslese]. And if you can still find the basic 2012 Donnhoff “Riesling” [what we used to call the “QBA” or the “Estate”], in quantity, at $19.99, then that’s your wine right there [it drinks like a Spatlese*].
I’d hit up all the major retailers in Massachusetts and see who might be sitting on a stack of quality 2012 Germans, in quantity, at your pricepoint. You might find something which is really fun to sip on.
*Or a cross between a Spatlese and Diet Mountain Dew with a few drops of fake lime juice thrown in for good measure. I’ve never tasted anything like the 2012s - they don’t have the elegance of the 2001s, but at your pricepoint, that’s a good thing.
For chocolate desserts, you just can’t beat a big thick inky-black Barossa Shiraz as an after-dinner port [they’re always real crowd pleasers at that point in the evening]. Unfortunately, Mollydooker isn’t available at that pricepoint in Taxachusetts, but these might work: