The Morgan Housel article is a good read.

We seldom sell stock. We frequently put appreciated stock into our Grantor Fund held at U.S. Charitable Trust. We then gift the funds over time to various 501.3c qualified situations mostly in our town/county/state. We usually do this moving of appreciated stock to the grantor fund in the same year we have a large tax obligation. In 2022 a stock holding was bought out. The ensuing capital tax gain was partially offset by moving some of our oldest Berkshire B shares into our grantor fund.

We also gift stock to our children and grandchild. This has been done for the past 23 years. Usually we gift stock temporarily beaten down in value. The allowed $16K per person gift per year using temporarily beaten down stock of a company is a good way to optimize future value for the recipient.

Like you, I had to start taking SS last fall and my bride has to start taking SS later this year. In three years Required Minimum Distributions will be our fate. We continue to own a business and are active in its operations, so we have income from the business. We also have rental property.

We find it is hard to change from an accumulator to a spender. The notion of a beach house or some other previously contemplated escape is no longer desired (too much work to keep up and we'd rather visit our grandchild) now that we are older (Medical records describe us as "Elderly").

It is easier to become a giver using appreciated stock via transfer to a grantor fund. Still, it is a hard decision to part with a holding likely continue increasing at 8 - 10% per year.

Good luck with your decision.

Uwharrie