I wish I would have started collecting Brunello and Barolo earlier.
If I were young, I would be raking a long, hard look at Barolo and Brunello right now.
Can’t taste everything before you buy, it’s impossible. So, look for a critic or two who calibrates with your palate. Also helps, when you do buy wine you can’t taste ahead of time, to try and make sure it’s one that you can pretty easily resell down the line, hopefully for a profit should you decide later you don’t care for it.
Keep an eye on Cellar Tracker. Biggest mistake I see guys making is they buy a wine that needs 15 years of aging, they drink too soon and can’t figure out why they aren’t bowled over. Give a wine every chance to succeed. Let it age properly, then stand it up a day before drinking, give it air, drink it with proper glassware at proper temperature.
Find and stock your cellar with stuff to drink while your other wines age so you won’t be tempted to dip into your long term agers before they’re ready.
Consider what you want to do with your wine. Are you looking for stuff to bring to a gathering of trophy wines, are you looking to pair it with food, do you drink it by itself?
If you’re looking to pair it with food, think about the types of cuisine you enjoy and then explore the wines that pair well. The types of wine that pair well with, say, Italian food might be different from what you might drink without food, etc. etc.