Deleting fields in Salesforce is a pain, one which I believe is only surpassed by trying to rename a field (and maybe a few other things), and I'm not aware of any shortcuts to make it easier.
There are two methods that I've used to find every place where a particular field is used:
- Using an IDE (Eclipse with Force.com IDE plugin, atom/sublime text with mavensmate), I can subscribe to every metadata type that can contain a field (customObject, which contains validation rules, workflow, visualforce pages, etc...). I can then do a global search for a specific field.
- When the above isn't enough, simply trying to delete the field in the Salesforce web UI will give you a list of places where that field is referenced.
I don't prefer the second method, as the UI that Salesforce provides when there is a conflict that prevents a field deletion is, frankly, horrible (in Salesforce's classic UI at least. I don't know if it's any better in lightning because lightning is still too half-baked for my company).
It'll tell you that the field is referenced in an Apex class, or a workflow, but doesn't tell you the name of the class/workflow/etc... or the location of the reference. You simply get a link (which is better than nothing, but is the absolute least amount of help that Salesforce could give).