Hey @Luke_Walrath1,
Currently it is not possible to set up a recurrent task based on a certain day of the month like in your case 2nd Monday of the month.
Here is an existing feedback request thread to upvote.
I’d say it really depends on how many tasks you will have in total and how your Asana Org/Projects are set up in general.
There are a lot of different ways to set this up and everybody has their own preference.
I recommend looking through some Asana guides and templates such as Free Meeting Agenda Template [2023] • Asana and also search this forum to see some examples.
Ideas can for example be found here, here, here
Could for example be a project template that you use or a task template that has subtasks.
You can also utilize rules to automate parts of the process.
Yes just be careful about this:
I hope that helps