Very interesting question. My strategy at current is buying in 3 or 6 of wines that I will almost definitely like and have a good likelihood of aging well–when there is a good deal on them. One for now, one for later, one just in case!
I don’t like spending more than $25 per bottle typically, so if a $100 bottle is marked $50, it’s still $50 to me. If it’s in my price range, regardless of where it started, and is good, I buy some.
I like the random ‘singleton’ buys occasionally. I may use those to fill out a larger order, or perhaps browse K&L Wines for regions and varietals I’ve never heard of. Rarely are the wines bad, and quite often they are brilliant and surprising. Why people go chasing $50 Cali Cabs or Chards and call them good QPR when there are $20 Nerello and Blaufrankisch is beyond me. Even when the wines are average in quality, they are intellectually satisfying as I must get out a wine book to read about the region and grape variety.
Usually I try to read CT to see if there are any notes on an unknown wine. I don’t care about the scores–I just try to see if the wine is interesting and has positive qualities.
Eventually I will have more producers and regions that were once unknown that I will buy in 3s and 6s based on random buys. There are some Loire reds and Cali producers I am not afraid to buy in some quantity for now.