I do my due diligence for any out of the ordinary purchase. Less expensive does not always equate to "cheap" quality. For all other purchases I find the least expensive and then buy the second least expensive.
That was my approach to ordering wine in a restaurant for about 15 years.
Now that the money is flowing like water, I've kicked it up to the 3rd or 4th cheapest wine.
If you don't skimp on the following you will have a pretty good life. I try not to.
Sheets (at least 400 count combed cotton)
Clothes (100% Wool or Linen suits, 100% fine cotton for casual)
Spirits (Kettle One, Johnny Black)
Meat & Produce
Cold Cuts (Boars Head)
Vacations (there are never enough of them, so make them count!)
Education for your children
Neighborhood/School District you raise your family and live in
And of course....Server for your highly trafficked website.
Someday, go to A&P and have them slice up some Hartford Reserve low sodium turkey breast. It tastes like you roasted it on Thanksgiving, not like a cold cut. Just superior quality. The Hartford Reserve low sodium Virginia ham is equally good.