This is what I use (primarily using self-hosted, open-source solutions where possible). For documents like invoices, correspondence, etc, I scan them into pape

This is what I use (primarily using self-hosted, open-source solutions where possible). For documents like invoices, correspondence, etc, I scan them into paperless-ngx.[0] You can apparently set it up to monitor an email inbox and automatically store certain emails or attachments using rules, but I just take the old fashioned approach of adding scanning them in and saving them manually. I backup all photos to a Nextcloud[1] instance. Periodically, I will go through all my recent photos and organise them. Travel-related photos go in trip-specific directory ("Travel -> [year] -> [trip name]"). Everything else just goes in a "Photos -> [year] -> [month]" directory. Unfortunately this won't help you find the photo of you wearing a cap unless you know where or when it was taken. I believe there are some AI-based solutions out there but I haven't tried them. For contact details, I store these centrally on Nextcloud using its Contacts app[2] (which uses vCard and CardDAV). I can then access it using any standard contact book software (I use the CardBook addon[3] for Thunderbird and Fossify Contacts[4] on Android). Similar for calendar - host it via Nextcloud (using CalDAV)[5] and access it from my preferred calendar software. Joplin[6] for notes (again synced via Nextcloud). The process is kind of half-automated, half-manual. I don't think there is a good solution to fully automate any of this stuff, particularly in the FOSS space. If you keep on top of organisation it's not that painful and doing things like organising photos and adding upcoming events to your calendar can be fun. Nextcloud is really good at acting as a hub for your data and speaking to a variety of clients using traditional, open protocols like CalDAV and CardDAV. 0: https://docs.paperless-ngx.com/ https://docs.paperless-ngx.com/ 1: https://nextcloud.com/ https://nextcloud.com/ 2: https://apps.nextcloud.com/apps/contacts https://apps.nextcloud.com/apps/contacts 3: https://addons.thunderbird.net/en-GB/thunderbird/addon/cardbook/ https://addons.thunderbird.net/en-GB/thunderbird/addon/cardb... 4: https://f-droid.org/packages/org.fossify.contacts/ https://f-droid.org/packages/org.fossify.contacts/ 5: https://apps.nextcloud.com/apps/calendar https://apps.nextcloud.com/apps/calendar 6: https://joplinapp.org/ https://joplinapp.org/