Qualifier/Disclaimer

This may be a very atypical question for this site (of all those I've seen, this question on superuser seems most closely related to mine, but the question was closed as off-topic there), but after reading through the list of all SE communities, I'm pretty sure this is the next best one (after SU) for my question. There may be a better one (maybe TeX & LaTeX?), though, and if you have suggestions for a better place to field this question, I welcome seeing them.

At its essence, I think this question is more about software (to facilitate writing under specific constraints) and less about writing per se, which is why I posted it to SU first, but perhaps someone here has some thoughts. Please pardon the length; it's been criticized as a "life story" question, but I'm not sure how I can pare it down. The length is more due to the detailed description of the very specialized task (which I think would be so abstract as to be meaningless without the specific example of why I want such a tool) than anything else.

The Background

For an important job application, I need to write a single coherent narrative of all my many professional situations over 20+ years, but I am severely constrained in the method of doing so. I'm guessing this is typical of many job applications, so there may be others with a similar question.

This narrative must read cohesively (as if it were written in a single document), but it cannot not be written in a free-form, free-flowing essay like a single document in a single text file. Instead, I am required to do my actual typing in form fields with strictly-enforced character limits. Some of the form fields limit the character counts to 60 characters, others stop at 500, 1,000, or 8,000. All of these various fields are then assembled, building-block manner, by the form software into a single "cohesive" professional history narrative that (based upon the character limits placed upon each form field) has an upper limit of 29,325 characters (about 7 pages in this form). I write cohesive in quotes here because although the software does indeed mash all the pieces together into a single unit, unless I take great care in writing all of the parts, the reader (a person I want to impress) is unlikely to think that the entire unit was written by the same person on the same day. That is, the whole narrative is quite likely to seem disjointed and/or rambling because of the piecewise constraints on how I must write it.

So I have about 50 fields to work with, and most of the fields are supposed to answer one specific question (what was your work like at this job), but some are more comprehensive and of course I'm trying to capture 20+ years worth of varying but related professional history so as to describe the skills and experiences of a single person in a coherent manner. I'd like to be able to use as much of the 29,325 character (7 page) space as possible because, after 20+ years, there's a whole lot to write about and as I approach this task (several rough drafts already), I'm constantly facing decisions on what to leave out for lack of space.

The Question

What application and configuration is most well-suited to this task?

I have experience with GNU Emacs, and what I'm envisioning with this tool is creating ~50 Emacs buffers corresponding to the ~50 fields of the form. Each of these 50 buffers could be configured to give me constantly visible, updated in real time, measures of character counts (as I type) while a 51st buffer would not even be editable but would instead just incorporate the contents of each of the others. This would let me have constant continuous feedback about my character count and limit for each buffer but would also let me read the entirety as a single document (even as I type).

In a sense, I'm already doing something like what I described above with Emacs, but the time lag between writing something (into the web app containing the job application) and seeing the entirety (by printing the entire application as a PDF) is minutes to hours, so this workflow process is very cumbersome and time-consuming and I can't help thinking there must be a better way. Maybe with some macro magic, I could do something like what I described with Emacs, but I thought I'd ask if there was a tool that already did something like what I'm thinking of here.

My main goal is to be able to constantly keep track of individual field character counts (with respect to their maximum limits) while simultaneously being able to read the entire narrative as a whole.

I realize this is a subjective question, with no single objective answer, but I've tried to craft it in accordance with the guidelines for good subjective Q&A, and I think it is definitively (if not objectively) answerable.

Product Idea?

If there's nothing that anyone can think of that facilitates this kind of writing, it seems to me like there might be a product opportunity here. I'm not a professional developer so I don't imagine I could do it myself in a reasonable amount of time, but I bet there would be a fairly big market for a tool like this. Whether conscious of it or not, people are constantly doing this task anytime they are applying for a new job.

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