Assuming that "external factors" you are referring to could be picked up by media queries, you could use them - adjustments will likely have to be limited to a set of predefined sizes.
Using JS you can change the height of the text, then simply bind this same calculation to a resize event, during resize so it scales while the user is making adjustments, or however you are allowing resizing of your elements.
If you want to set the font-size as a percentage of the viewport width, use the vwunit:
#mydiv { font-size: 5vw; }
The other alternative is to use SVG embedded in the HTML. It will just be a few lines. The font-size attribute to the text element will be interpreted as "user units", for instance those the viewport is defined in terms of. So if you define viewport as 0 0 100 100, then a font-size of 1 will be one one-hundredth of the size of the svg element.
And no, there is no way to do this in CSS using calculations. The problem is that percentages used for font-size, including percentages inside a calculation, are interpreted in terms of the inherited font size, not the size of the container. CSS could use a unit called bw (box-width) for this purpose, so you could say div { font-size: 5bw; }, but I've never heard this proposed.
I've given a more detailed answer of using vw with respect to specific container sizing in this answer, so I won't just repeat my answer here.
In summary, however, it is essentially a matter of factoring (or controlling) what the container size is going to be with respect to viewport, and then working out the proper vw sizing based on that for the container, taking mind of what needs to happen if something is dynamically resized.
So if you wanted a 5vw size at a container at 100% of the viewport width, then one at 75% of the viewport width you would probably want to be (5vw * .75) = 3.75vw.
I used Fittext on some of my projects and it looks like a good solution to a problem like this.
FitText makes font-sizes flexible. Use this plugin on your fluid or responsive layout to achieve scalable headlines that fill the width of a parent element.