This is a great and understated point. Having the money to spend on an item is one thing; having confidence in that purchase is an entirely separate endeavor.
Throughout the years the vast majority of my Pokemon purchases have been under $200. Around Covid era is when I picked up my first “most expensive” card, which was a PSA 9 1st base Gyarados for around $1k or so. That was a lot to spend on a card for me at the time. Later that year I added Alakazam and Zapdos to the list, but wound up selling all 3 for more than I had paid to cover some other purchases.
Used to have a pretty big MtG collection of Commander/EDH decks, but our local scene died out and there was no point in having nearly $10k word of decks that I wasn’t ever going to play with again (nearly all of these cards were bought well under 50% of what they became to be worth since I was a player for so many years). Wound up selling it all to a vendor at GenCon a couple years ago for $7k cash, which was very fair. The very next month I bought a Blastoise PSA 9 1st base set for $3.8k I think. To this day that’s the most I’ve ever spent on a card. Turned out to be a great move since that card is way up from my purchase price. One day I’ll add more to the base set collection.