Automated dependencies/estimates and timelines?

[Quinn Campbell]

I'm very new to Jira so forgive if this is silly and I'm missing an obvious button. I have figured out how to automate and link our tasks that come through with a new form request. New request -> triggers new issuse-> Issue details are filled out (manually by user, still trying to figure out how to get more info into the request form) -> Issue is moved inline with workflow (manually)-> triggers a bunch of subtasks that are standardized based on where its dropped 

now my several questions

Task timing (original estimate?) - I believe the estimated timing of a task should be the field called original estimate, but when I assign an estimate of time it doesnt come through in the automation. That field is blank when its created. Anyone know potentially why? Is there a minimum amount of time allowed or something?

Timeline viewing dependencies - I have figured out the "linked Issues" field and gotten that to work for me linking each item to the item above it, and see the links in the timeline view, but the subtasks are stacked on top of each other rather then cascading in displaying dependencies. How do I get them to acutally show in a chronological/cascading order horiztonally in the timeline automatically rather then having to drag them manually.

I feel like these 2 issues might be linked but am not sure. 

I have other questions about what is possible when generating reports (am I limited to pie charts and other simple graphs or can I output a spreadsheet of data), if its possible for a request to trigger an epic instead of an issue, and how do I allow for a more indepth request form, but will get to those later. 

Thanks for the help!

[Quinn Campbell]

I meant to attach a picture of what I meant by stakced vs cascading. First pic is how it comes through, second is an example of what I would like (was done manually)