No No's for Deal Lovers

Following yesterday's exploration of why some of us are faithful PSAWSWLD's ("price-sensitive affluents, wealthier shoppers who love deals", a sought-after Walmart market segment), it is important to point out there are lots of situations where playing this game is a bad idea. Obviously if one is on a limited income, there is little choice. But if one has disposable income sometimes it is wise to just spend it.
For me, the basic principal is if there are other people involved, think carefully of the impact of the behavior. I recall my mother, whose family had lost their business during the depression and went from prosperous to poor, always shopping sales with me. By then we were middle class, but being taken straight to the clearance offerings first sent me a clear message: I was unworthy of full-priced clothing. It made me feel guilty for wanting the pretty dresses displayed in the store window. That was not my mom's intention; she simply had retained a habit when it was no longer necessary. Children need to be guided, of course, and a shopping trip can surely include the sale rack, but heading straight to it takes the pleasure out of the experience. If you give kids a clothing allowance and they choose to stretch it farther, more power to them. But then they are choosing that option, it's not parent-driven. I think the aesthetic of shopping is especially important for life cycle events, when the clothing choice is part of the ritual. There are plenty of other opportunities to shop at thrift stores and discount emporiums.
Gift-giving is also a time to step up to the plate and do it right. I remember returning a wedding gift and discovering it had been purchased on sale. We received $8 to spend at Bergdorf Goodman. Tacky. Regifting is fine for random hostess gifts, IMHO, but do check the bag or box! We were once given a lovely bottle of wine complete with the note to the givers, not to us, inside the gift bag.
If you are a person of means, donations are a place to be generous. Set a goal for yourself, like tithing, and don't sweat each contribution. If you are giving a donation in someone's honor, this is particularly an opportunity for generosity. A tax deduction even comes with it. Know, too, especially with online donations, the recipient is sometimes informed of the amount. My current favorite gift is a large number of trees from Trees for the Future - who wouldn't enjoy knowing 1000 trees had been planted in their honor? (This only costs $100.)
Dealing with low-income workers by skimping on their wages has a name: exploitation. We knew a family who always rounded down on their babysitters' hourly pay. Yuck.
One big area when being too focused on a deal is plain foolish is when your time is valuable, and you just want to get the damn thing done. Go for it!