Welcome to the forum!
I guess you must have a reason for not explaining more about your project, which I can totally respect if it just can't be shared. But the more we know, the more likely we can offer best solution or potential solutions. In any case, I have some questions, before I can consider how to do what you want.
First, it looks like you are rotating the path, making a couple of edits, and rotating it right back where it started. Is the reason for doing that because it seems easier than scaling along the 330° plane or vector?
Next, why do you scale it twice? I can't think of a reason for that. Is it something to do with the stroke? You should be able to just do it once (unless there's some info I don't have)?
(now my path is gone, instead I have a path tracing the outline of my stroke)
As far as I can tell, these original paths must be closed and filled, without a stroke. (Otherwise, you wouldn't be able to add a stroke to them.) (because almost always, an open path will be already stroked) So what you had originally was a path tracing the outline of the shape.
When you do Stroke to Path (for your original closed paths) you not only have one path outlining your shape, you have 2. Did you realize that? Stroke to Path converts a single,
closed path into a compound path consisting of 2 subpaths combined (inner and outer edges). Stroke to Path converts a single
open path to a single closed path.
So if your ultimate goal is a single path around a particular shape....if it's already a path, you just need to add a stroke to it. If they are vector
shapes (rectangle, ellipse, star) you just need to do Path menu > Object to Path. Then just add the stroke.
After that (according to your steps) you would just need to scale them. And there is a way to scale in one direction. And as Moini says, you should be able to select them all at once, and scale them all at once.
I realize I did a lot of surmising there, so if I came to wrong conclusion, please explain more about your project or immediate goal.
Edit
To answer your question, it is possible to use scripts to perform a sequence of commands, repetitively. You would need to know how to write the script yourself (unless someone volunteers to do it for you). Also, Inkscape has a command line feature, which potentially could be used for this kind of thing. But again, you need to know how to use the command line, or be willing and have time to learn.