I have encountered many critical limitations because of numerous instances of not being able to reenroll objects into workflows using standard enrollment criteria. The workarounds are very inefficient and complicated.
RollUp properties cannot be used to trigger a workflow reenrollment when using the “last updated within” option. (this alone would solve all my issues)
Association Label changes also cannot be used to trigger reenrollment which is the reason I would have used the rollup property that counts the number of associated contacts.
I am trying to create a workflow for a custom object that enrolls when associated contacts change that have specific labels. There is absolutely zero options do this within Hubspot without using a private app and custom code using webhooks. Even then, webhooks aren’t setup to trigger based on association changes between standard and custom objects so I even have to find a workaround within my private app and webook to create a queue of my custom objects based on the object recently changed property. This is VERY inefficient and a waste of time and resources all because there is no way to reenroll objects into Workflow based on normal criteria.
100% this past 2 weeks alone I have hit a brick wall on SEVERAL operations that are now manual because of reenrollment limitations.
Example: Simply updating whethere a client (Company) is active or inactive status (custom drop down property) based on a matchng custom dropdown deal property of inactive or active is impossible due to reenerollement limitations - this is craziness to me. If any associated deal = Active, update company dropdown to Active and if NO associated companies are Active turn Inactive. But nope because associated objects can’t trigger enrollement 
Rollups don’t work in these situations I have exausted options with Support (Carlos you’re a gem). Other similar processes that need to be executed as well this isn’t the only one. Plz Halp remove manual tasks from my day with this improvement 