I do this for some yearly tax stuff, as the big issue for me is that it was a year since I did it last and getting started with a complex and boring thing is hard

So I built a script that tells me what the first step is. When it's done I run the script again and it tells me what to do next. Often the first few steps are "download this CSV from the bank" so the script can detect I've done than and go directly to the next step when I rerun the script

The reason I have a script I rerun rather than a "press enter to continue" is because it then only keeps persistent state, and I can easily do a bit every day until done

A common pattern is

    if ! [[ -e checked-all-the-receipts ]]; then
         echo "check that the receipts match the list of expenses, then"
         echo "  touch checked-all-the-receipts"
         exit 0
    fi

Then over time, I have automated some parts and added some checks. E.g. when I have downloaded a CSV I can check that the format looks right before considering the step done. I've added some autogeneration of documents I need, built a python script to add up transactions and check the that the totals match etc