We're probably alike in that we are surrounded by people who aren't as tech savvy as we are and sometimes we want to solve a mutual issue with a solution from our geeky world that may prove itself challenging to implement. Here at home we're not adept calendar users, yet we were staggering to share errands and reminders, so I came up with a set of easy-to-setup implementations that helped us keep tasks in check and may help you sync with your family.
I tried and failed multiple times to push apps into my family members, and I learned that I would most likely continue to fail if I persisted to force my personal workflows into people who use 3-4 apps a day. The key, I figured out, was to reverse the process and tweak the apps my family was already acquainted with.
The chosen app to share tasks and errands was, obviously1, Apple Reminders, since it comes with the device, it is easily accessible from Siri and has a simple interface to share lists. The interesting part of working backwards is that the hiccup now is how to make this fit into our overly complex task management systems.
There's another issue though, if the person you're sharing your list with doesn't already use Reminders, then there's a good chance your efforts were in vain. To help building the habit, you want to add the Today Widget for reminders and you may have realized it is already activated, but showing none of the tasks your shared because the widget only displays reminders with a due date.
The only workaround to that is to use a third-party app to handle the reminders in the Today Widget and the best one is definitely GoodTask. Sneakily install the app and configure its Today Widget to show your shared lists and done.
If you use Omnifocus, you may consider to use the option to capture a Reminders list. However, this option moves the reminder to a "Captured by Omnifocus" list afterwards2. In the end, we gotta duplicate the original reminder into your Omnifocus, and I've been using IFTTT to do that.
Unless you use Gmail, you won't be able to use MailDrop to silently add a new task in the background, however, I believe we would appreciate a notification whenever a new task is added to our shared list, which is why I use the fantastic Launch Center Pro integration with IFTTT to triage the tasks I'll add to Omnifocus.
There's not much you can do beyond that since Omnifocus' URL scheme is stagnant for at least 4 years and Omni seems more interested in styling Omnifocus these days, so whenever a task is completed in Reminders, you'd still need to complete the duplicate in Omnifocus and vice-versa, but this is an obstacle you'd face with any app.
Among the multiple parameters offered by 2Do's URL scheme, you could include
dueDate, unfortunately, IFTTT doesn't share that information as an ingredient for your recipe, so we can't use it. You can, however, use the List name to add the task directly to a homonymous list.
We can also create a recipe that will notify us whenever a reminder is completed in Reminders, so we can run an URL to open its respective list in 2Do. It's not as good as completing the reminder for us, but at least takes you to the right place.
Then we can start with the real hack and complete the respective tasks in Reminders when we're done with them in 2Do. How? Pythonista, which has access to the built-in Reminders. So we gonna attach an action to our reminder when we add it to 2Do to trigger a script that will look for our reminder based on its list and title and mark it as done.
Here's a video of the full procedure:
Maybe we overdid ourselves here, but hopefully no one will forget to pass in the grocery store to buy milk or cook the dinner because someone will be late and, in the end, when you're working with people that are not as crazy about technology as you are, don't push your habits, remember, you've been tailoring them for years to be perfect for you and, as you may already know, it is very hard to change a habit, either good or bad.