Shooting portraits for a long time, and especially with most of my clients being women in their thirties and older (they are the ones with money and are buying photography), this is one rule that has never steered me wrong: Roll back the last five years.
A woman (and men too) who is thirty would rather look 25. A woman who is 50 would rather look 45. A woman who is 60 would rather look 55. I think it takes about five years for people to become comfortable about what they looked like five years earlier. That means eliminating recent age signs such as finer wrinkles and anything that is temporary. People of color collect tiny age-related moles the way light-skinned women collect age spots, so you can remove most of those age-related moles. Almost everyone of every age will have horizontal "necklace" creases around the neck. I always remove those.
About the only people over 30 who are comfortable with the appearance of their age are people in their 70s and older--at that point they get the attitude of "I worked hard for these wrinkles." Even with them, there is another danger:
The camera emphasizes defects. Only image professionals like models and actors can normally look in the mirror totally objectively and can see what a camera will see. For everyone else, it's usually a rude shock. That's why so many people say, "I never like my pictures."
When you interact with a live person, the constant motion and 3-dimensional view keeps you from concentrating on defects--you're engaged with the entire personality. But when you fix the image to a 2-dimensional surface and remove all other input, the blemishes are emphasized. That means you need to soften or lighten all blemishes--even Cindy Crawford's mole--to some extent because they will be more obvious in the photograph than in person.
Also, some bulges and wrinkles are a result of the pose, such as the common "over the shoulder look" pose, which usually results in deep neck creases even in young subjects. In the old film days, we'd hide those with careful placement of the hair--a compromise and a shame if the woman had a beautifully long neck. At the high end, an expert negative retoucher would handle it. But today, we can pull the hair back to expose that lovely neck and then easily take care of the creases in Photoshop.
With a bit of experience, you'll be able to pick up on what to remove and what to soften. You get a feel for what marks are "character" and what are marks of mere wear and tear. I generally do not ask because my clients come to me expecting me to know what to do. I've never had anyone complain about too much work, but I've had a few look at the previews and ask me to do even more. People know you can 'Shop out defects, and they expect it more and more these days.
I photographed one lady in her 70s who was utterly delightful to converse with. She was witty, had a quick smile, and had the clearest and bluest eyes ever. But she was also heavily wrinkled. In person, you were so engaged with her charm, her eyes, and her smile that you didn't notice the wrinkles...but in a photograph, the wrinkles would have dominated everything. So I had to pose and light her to emphasize her eyes and smile, and then follow that up in Photoshop to "emphasize the positive and de-emphasize the negative." No, I didn't try to make her look 25, but I tried to re-create the experience of engaging her in person.
I had a client not long ago who had had a mild stroke that had left one side of her mouth slightly paralyzed, and her concern was that I take a picture that did not show it. To do that naturally, I chose to photograph her with only slight smiles that could most naturally be adjusted in Photoshop--trying to fix a big grin would have been possible...but nobody ever saw her that way.
As a beginner's rule of thumb, if you didn't notice it when you looked at her in person or through the viewfinder, remove it from the photograph--it was not part of the personality you experienced live.
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