Wow, I guess paintings are the blow-out gazingus pins of the truly frugal! I typically think long and hard about any purchase over $100--less than that, I'm too prone to fritter it away for some things (not Starbucks or food, but books, cheap online classes, etc.)
But one of my very favorite people and places is the artist Stephen Huneck/Dog Mountain in VT. They always have a March Madness sale. Well, my birthday is in March, and the year that I turned Medicare-eligible, I thought about the huge savings I was about to get from not having to pay full-boat commercial insurance, and, very uncharacteristically, I decided to blow my first month's savings on a numbered S. Huneck woodcut. $800. But I do love that woodcut and I look at it every day, happy that not only do I get to enjoy it, but I supported a wonderful organization.
As far as bargains go, I tend to be also of the mindset of "it's better to not buy than spend time tracking down the cheapest way to buy." People who are constantly bragging about their nickel-and-diming can get a little tiresome. However, I do love scoring a good bargain when I find them!
ETA: Well, looks like I could always get my money back if I get desperate for cash! My woodcut has appreciated in value!
https://www.dogmt.com/She-Sings-A-Lo...g-Woodcut.html