A good value bottle of Whiskey sits around $30-$50, and you can easily spread that single bottle over at minimum 20 servings. For a few dollars, if you enjoy it, that's a pretty good value.
As you get more expensive, you tend to get more distinct and nuanced. Smoother hard liquors, more interesting flavors, etc. We once did a tasting flight and one tasted literally like camping outdoors with the smoke and wood. Another tasted almost like honey. So, to me, it's not that expensive and opens you up to an interesting and exciting landscape of flavors.
If you're comparing to prices on a menu at a restaurant, then it's completely outrageous that a single glass would cost as much as your entire dinner. And there I agree, it's completely skewed.
Granted, after a certain point (about $200 for me since I'm still a relative newbie. $1k is getting outrageous imo.) you're just chasing popularity, hoarding as a collection, or showing off your wealth. There's some amazing stuff, and for those trained and really knowledgeable and deep into the hobby it's worth it as they tease out all the little nuances. But just like buying a >$1k bike, for the average person you can't take advantage of the extra value and care that went into the product.
I'd put this price at around 2500. The better shifting from a decent group set makes a huge difference in a new rider's ability to enjoy the ride. It's hard to enjoy a ride when your chain keeps dropping and you cant shift through your gears. Though, I really wish someone would come out with a mass market Ultegra spec'ed decent geometry steel bike for ~1k.
A big part is finding and trying cool stuff, but I'd guess every ~3rd bottle I buy is GlenDronach, so a big part of it is also just loving a couple things. Like: if I buy a dry-aged prime ribeye, it's expensive, but I'm not looking for something "new" (that would be worrisome) so much as something enjoyable and a bit scarce.
Important to keep in mind that it's not "alcohol", it's whiskey. It would be weird to spend this kind of effort on vodka or even gin.
Lagavulin 16 - I hadn't had much scotch before I tried it. Very confusing, as I initially didn't like the peat, but was more and more intrigued by the same thing that turned me off to it. Kind of the same experience I had with IPAs.
Tamdhu - I really liked this one. Felt easy to drink, familiar, and comforting.
Balvenie Caribbean Cask - Pretty bad. The rum notes made me feel nauseous.
High West Double Rye - Really good. "Fresh" for lack of a better word (but I had a second bottle years later that was horrible so who knows).
Pappy 15/20 (before they became $$$) - I thought the 20 was okay. Tasted like a mellowed out Buffalo Trace. Really liked the 15--flavorful, hot, and just the right amount of sweet.
Dollar for dollar, there's probably no better value in Scotland than a GlenDronach 15, and you really can't go wrong with any GlenDronach, from 12 to 23, with an age statement.
Aberlour A'bunadh is Aberlour's no-age-statement high-cask-flavor expression and it's pretty cheap (like $50?). If you buy it and really like it, there's a whole world of wine-casked Speysides you can go explore.
I am a fiend for cask-y Speysides but I haven't really liked any of the Balvenie stuff (even though Balvenie is one of the cooler distilleries).
I'm working my way through a Tamdhu NAS Special Edition which I'm liking a lot, so our tastes may be similar.
If you're less into sweetness and wineyness and fruitiness and more into grain character, I like Springbank a lot.
The good news about American whiskey is that spending money on it is the wrong approach. The right thing to do with American whiskey is to buy bottom-shelf bourbon and rye, preferably from brands that have a bottled-in-bond expression of whatever it is you're buying (or just buy the bonded expression itself if you can get it). So: Very Old Barton, Heaven Hill, Old Granddad, and Old Forester. These are, like, $30 bottles. Also buy a Four Roses and a Wild Turkey.
Don't buy premium-priced American whiskey until you've tried enough "cheap" whiskey to know what you liked and (importantly) don't like. You can live on the bottom shelf of bourbon and be a happy drinker for a long time, and you get snob points for appreciating a cheap Heaven Hill while "hipsters" pay $60 for an "artisanal" "craft whiskey" that is really just a bottling of MGPI.
Later
A lay-up pick in your price range is Redbreast Lustau, a sherry-casked Irish whiskey. Over-the-top wine notes on top of an already super drinkable whiskey.
Man.. It really comes down to preference. I find Old Pulteney 12yo to be one of the best values out there (I prefer the 17yo, but it is for sure more pricey).
The annoying way I look at it is that if I'm going to pay 3x as much as I pay for VOB to get a scotch, I want something more interesting than a nicely balanced whiskey with some spice and some caramel notes. That's all well and good, but I can get that from Four Roses.
But one thing I cannot get from American whiskey is nicely balanced whiskey with powerful wine notes. As a rule, American whiskeys are aged for a relatively short time in new oak, and Scotch is aged for a long time in used barrels. So Scotch distillers are experts at imparting flavors from different casks, and that's kind of what I'm paying for.
That, or I'm paying for smoke and phenols and brine, which I'm sometimes in the mood for, but mostly I avoid.
I tend to not like heavily sherried Scotches (sherry-bombs), preferring oak, smoke, peat, brine, and nutty flavors. Sounds like you enjoy the wine/sherry though. Luckily there are plety of options out there for both of us.
Sláinte!
That said, drink a bunch of cheap whiskey. Basically all American whiskey can be found in cheap expressions that capture the things that you like. Learning that you prefer Wild Turkey to Four Roses (for instance) gives you information to move up the price board.
I do feel that many of the brands are priced by pure marketing (ie whistle pig). But some are quite good.
FYI some of the high West varieties are MGP product mixed with High West own distilled product.
As for transience, you can stretch out a bottle of spirits over months. And hopefully the wine would be enjoyed synergistically with some great food.
All that said, there are a thousand good/interesting $15-25 bottles of wine to chase if you're wanting to get into that, and IMHO Veblen goods are stupid.
How do you figure? Food is at least as transient. A several hundred dollar bottle of whiskey can last years.
I get collecting. I love it. And at that level I understand. But from a pure enjoyment level I do not.