In the case that the user dspace (which runs the crontab tasks) does not run the Tomcat process also, then it might lead to changed permissions in the assetstore directory. This mainly happens when a new bitstream is added to a new record, or re-added to an existing record, where the code is executed as the user dspace and therefore changes the permissions in the assetstore path directory. It may not alter every subfolder's permission, but at least it will change the permissions in the directories that comprise the path to where the bitstream will be finally added. This is accummulative and it might lead to a lot of portions of the assetstore's prmissions changed, depending on the number of the added bitstreams. This is certain and it also happened to our installation, when we used to run the tomcat webserver as the Tomcat user, and I had to reset the permissions periodically. In the end I switched to run the Tomcat process as the dspace user and I never had to reset any permissions in the assetstore dir.
Another reason this might occur is via the crontab tasks and most probably the filter-media task, but I am not very sure about this.
In any case, I wouldn't run the Tomcat webserver as a separate user from the one owning the assetstore dir. In case you wish to keep that then you can use crontab once or twice a day to reset the permissions to Tomcat8 user.
-Fk