Brandy isn't about grand labels or super pricey bottles. It's first and foremost about having a good time and making social connections while drinking something that tastes good to you. Then, one can, if one feels like it, make it an exploration, a discovery.
Lots of drinkers are coming to brandy from another category (often whiskey) and might not know "where to start." I believe the answer is "just start somewhere." Don't obsess about the stuff, don't over-research, and don't freak out as to whether this first bottle of Armagnac or Calvados is good enough or if it is too cheap and you should spend more.
First off, some of the most memorable spirits I've encountered weren't the most expensive ones.
Second, it is super important to be open-minded and willing to try out several things before making an opinion for oneself: by that, I mean one would likely not decide whether one likes "red wine" based on that random "Merlot" one got poured on board of that coach flight.
So, pay attention to what you’re drinking. Does it taste good to you? Do you like it? That’s #1. If you do, can you say why? If not, it’s totally fine. But knowing why one likes a specific spirit (or not) helps in navigating the world of possibilities within that category.
One could take this a few steps further by learning what that stuff is, where it comes from, who made it, and how. Are the makers cutting corners, or is there an authentic, artisanal touch to it? Does the brandy reflect a sense of place, a tradition, a story? Understanding the 'who', 'how', and 'why' behind a spirit adds depth to your drinking experience and allows you to get a better sense of what you are drinking. Having that context allows you to understand why that stuff was $35 when that other thing in the same category that you were debating getting instead was three times as much. Maybe one was made by a négociant and bottled with additives at 40% alc when the other was made by a family, without corners cut, and at cask strength? (Again, marketing has been around for a long time; pricier does NOT necessarily mean better or older or more artisanal.)
When I am drinking anything really (besides water), the main thing I pay attention to is: "does this liquid have a personality?". I don't want to think too much about it; I don't want to contemplate the beverage for hours. I want to see if that liquid naturally made a positive impression on my brain. If the answer is "yes," often I do want to go deeper, but it is not a prerequisite.
I am just not interested in ingesting something boring.
Example: new to Calvados? Never tasted the apple stuff from Normandy? There are plenty of cheap options out there to dive into it. Take an entry-level VSOP Boulard or Pere Magloire, for instance. They are a decent introduction to Calvados, totally serviceable brandies. They might not blow your mind, but they are stepping stones in understanding what this category has to offer. Just remember not to judge the entire world of Calvados based on that one bottle you picked up, not knowing much about the stuff, and chose mostly based on its price point.