Hi @TChappell5! I believe, no matter which tool you use, it’s going to be a lot of upfront setup followed by small refinements. My encouragement would be to choose the method/tool that makes most sense to you, that gives you the reporiting capabilities you want, and then put in the effort to make it work for you.
Depending on what level of HubSpot you have, you may also look at the tool called Sequences which kicks off a routine sequence of events. It still may be a lot of setup for the processes you’re talking about but once this process is setup in whichever tool you choose, life will be much easier.
A thought I had while reading your question is grouping “tasks” by week (for example). So, instead of having a seriese of individual tasks, you could have a Task with a list in the body for all the items that need done the first week, second week, end of the first month, etc. Whatever grouping of time makes sense. Maybe it’s even first day, second day, end of first week, so it’s granular at the beginning and then stretches out.
No, HubSpot does not have a checklist idea like, for example, Monday.com has. (HubSpot Integration – Support) You may have to train your people to continue to add notes about what they did and when and only check off a Task when all the items are noted.
I’m am not familiar with this at all, but, Customer Object Cards may be another things to look at and perhaps work with a partner to build for you if it’s out of your wheelhouse. Create custom object records
Hope something in here helps you move forward.