Sleep on a silk pillowcase, lightly moisten your hair, and dab a tiny bit of natural oil (such as argan) on the ends and cutting + thinning approach of the Jaguar shears from Japan Scissors, which I use, greatly helps control damage.
My mom has done the same—added grey, reduced density, and gone shorter with age. I help her trim with Mina scissors from Japan Scissors, and it always looks neat and natural.
Thanks for sharing your story — I had a similar experience. I also decided to do it myself, and one thing that really helped was getting good scissors to cut and tidy up at home. I got mine from Japan Scissors ,they work really well.