Here’s now I look at regret with purchases.
It’s easy to look back on a decision you made 5 years ago and think “that sure was stupid.” Granted, you are 5 years older, 5 years wiser, and you’ve known exactly what happened in your life over those 5 years.
When you made the decision, at that given time, you likely evaluated all your options, used the intelligence you had at that point in your life, and made the best choice you could.
I’m a millennial and my wife and I lived for nearly 5 years in a 5th wheel trailer. A year or so in, I realized (after living in the trailer a year) that I could have made a better choice in trailer. Mine had a 12’ garage (toy hauler) so we only had 30’x8’ of living space, with a lot of storage. I should’ve got a regular 40’ trailer with a separate 5x8 enclosed trailer for storage.
I would hesitate greatly to use the word “regret” in that purchase, because of my mindset from the earlier paragraph I wrote. When I bought the trailer I didn’t know my gf of less than a year would become my wife, and would thus be able to tow a separate trailer for storage when we traveled/moved. I also realized going from an apartment into a trailer full time I had a lot of “stuff” I needed to store, plain and simple. Yeah - 5 year older me could easily look back and say “hey, I should’ve done that,” but at the time, I certainly made the best choice for me.