re: Am I overthinking my résumé and cover letter?

Bullet points and concise text should be used as much as possible. If you get an interview, don't print your resume on stock white paper, get the off-white linen resume paper and the matching envelope.

There were over 200 applicants to the job I landed last September. I had the experience to get an interview, but researched the company and position ahead and knew who would be interviewing me. Then I brought a copy of my resume as described above to each person I interviewed with. That attention to detail throughout is what will set you apart from other candidates.

Get a recruiter.

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Yeah it's not that I'm listing too many jobs or experiences, but I provide details of what I accomplished and what I did at each job. I mostly list things that match up with the posting.

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I didn't read every responses so sorry if this is repeated advice, but if you're going into details about past jobs on your resume, make sure those details aren't repeated in your cover letter and vice versa.
Hiring teams don't want to read a long cover letter and then see a resume covering that same information.
My advice is to shorten the letter to cover just a few interesting things that draw them in and highlight your career. Then leave more of the job details to the resume.

I can tell you that if you are submitting 4 pages of stuff for someone to read, you are wasting your time. Hiring managers generally have quite a stack of resumes and cover letters and they absolutely aren't going to make it through anywhere near that much text.

keep your resume to one page and your cover letter to a few paragraphs on a page.