On our AR ZOOM call today, our speaker, Andrea Bedard, prefers Folio. I am going to try it as well.

TAke a look at WiseAgent.com
Checklists and note fields that are searchable are some of the features that make WiseAgent agile.
I used TRELLO but project/task management software like Trello is overkill for agent work.

I wish you all the best with this. No doubt you will receive many suggestions from other AR members.

I own and manage a boutique brokerage of one. The systems I use are self-created and work well for me. The only person I assign tasks to is ... me. 

Hubspot may be worth checking out.  It's geared towards project management (though many use it as a CRM) and has dates, Gantt charts and the like.

Keller Williams has their own proprietary product for such things.

I use google calendar, however I have heard of others who use the fuctions for this included in some transaction software like dotloop, command, skyslope, and others to do this.

I am a fan of Folio! It may not be exactly what you are looking for, but I've found it very helpful. You can create a timeline, add comments to each milestone, attach documents and share it with parties involved with the transaction. When it's all done and the transaction settled, the entire thing is archived (in case you need to come back to it later) and with a yearly subscription you can download a pdf of all your emails. 

The only thing I am not sure of is whether or not you can assign tasks. 

Thank you Debe Maxwell, CRS for making me aware of this question. Very timely!

So happy to be retired, parked and reading! Good luck!

Blog about your selection.

Compare slack. https://slack.com/

I don't have a good suggestion, wish I had a perfect system. Whatever you choose, the key is to use it and be consistent with it. I find that some of the systems are too time-consuming to manage; require a lot of minute input.

This is always the question of the month. What CRM do you use? Can't really give any good advice.