@Andrew_Enright - you’re correct - but I think you mean 1000+ records in a Milestone table?
A Milestone table would allow you to monitor the progress of each Milestone and produce the Calendar you were looking for - which could be filtered in many ways as you know.
My thoughts on auto creating milestones for each new job is that Zapier would be triggered by the new job record and would then create the milestones. In my experience, this is often not as simple as it sounds because there are probably different types of Job and each would have a different set of milestones with different timings. If this set of milestones is totally variable then I think they would best be created manually - but you could save some effort by having a table of Milestone Types from which you could pick the milestones you want for a particular job.
Here’s an example I’ve been playing with:
The calendar is filtered showing only outstanding Milestones - whereas the grouped view is ideal to use for tracking progress and ticking things off as they get completed - notice I have grouped by Client and then Job.
If you wanted to automate set up of standard Milestones and these varied by the type of Job, you could add a Job Type table and have a field which would contain all the relevant standard Milestones for that Type. Zapier could then read this list and create them for you. Note that you would need to add some timing information (i.e. how long after the job start should a milestone typically happen) and also consider if the 5 or 15 minute delay on this happening via Zapier is acceptable (hopefully Airtable will enable Instant Zaps at some point to get round this though).
I have set up this type of Zapier integration before for a client and it seems to be working quite well for them.