When? For me, it's early morning and then early evening; and best after a workout at the gym or a brisk walk with the pooch.
How? The more personal the communication is, the better.
One of my daily habits is to check the new listings and any price alterations of some 'hot' listings I keep note of. Luckily, our real estate board has a very easy to use sytem that manages automated searches for clients. And, if I send a copy of the search to myself, then I am updated when my client is; ready to go.
For example, this chart of Sale Price to Original Price ratio for Saanich East single family homes, 2-3 bedrooms, 2-3 bathrooms took about 30 seconds to generate:

It's so important for me to be there with answers for my clients when they call or email - the combination of our Board's computer system along with the power of the smartphone makes it possible. And, if I don't have the answer then and there, I can find it quite quickly. It's all about keeping in touch, being top of mind, etc.
Keeping in touch with a more personal approach - I began sending out note pads with hand-written notations on the top page. My client receives a greeting or a tad of info, plus a free note pad. Works great.
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