Here's how I do it while preserving sanity: DSLR photos are for art, not memories. I use only my Android phone for memories (among other things). I have a dai

Here's how I do it while preserving sanity: DSLR photos are for art, not memories. I use only my Android phone for memories (among other things). I have a daily job that transfers photos from my phone to my PC. Once a month, I copy all the photos/videos of the previous month into a directory. I fire up a simple Flask web app I wrote that builds a page showing all the photos/videos that are in a directory. Under each photo/video, I have: - A checkbox on whether I want to keep it - A textbox for putting a caption. Here I write whatever was going on that day (or when I took the photo) - A field for entering tags (plain text, tags separated by commas). When I hit a button: - It copies all my selected photos/videos to another directory. - In a static site generator, it creates entries for each day there is a photo/video. It adds rich text (e.g. Markdown) to the SSG entry with links to the copied photos/videos, and "captions". The tags I had entered apply to the blog entry/day (not to the individual photo). That's it. I'm done. Separately, I have a daily cron job to build the site, and make a new page showing me all entries for today's date (i.e. all photos/videos taken on Jan 27th). This way I can see what I was doing on this day 4 years ago, etc. I keep whatever I want. If I go for a monthly book club meeting, I take a picture of the building it's in and note down what book I read. It's very manageable. At one point I had a bug and didn't update it for several years. When I finally got around to fixing the bug, it didn't take long to catch up on that backlog. I don't curate my DSLR photos. No time for that. It's why I don't use it for memories.