Tagging tasks with in a list help

I am only starting with Obsidian, previously I used zim wiki and have built a good work flow which now needs to be recreated or changed.

Before I could tag a check list with a key word header and all items in the check list would have the tag applied. Below the examples use the syntax from zim, the @ creates the tag.

TODO: @house_task
[] item 1
[] item 2

TODO: @house_task @outside
[] item 3
[] item 4

In the above example all four items would tagged with house_task and searchable by that tag. While only items 3 & 4 are tagged with outside. This is the behaviour I am trying to reproduce, with the most important feature being the tags have to be dynamic. A list of predefined tags will be very limiting in how I work.

Any suggestions on how this could be achieved? I am open to changing my work flow but I just don’t know how to achieve the desired affect.