Unsuccessfully searching for a job for almost 2 years.

I should start off by stating that I am not unemployed. I have been working for a little over a decade as a NYC Public School Teacher, and I still have that position. I am 37 years old, white, and male.
I am a Technology Teacher and a Technology Coordinator within one school building. The second position involves giving Tech Support and helping teachers incorporate new software into their classroom, as well as weighing in on the technology strategy for our school.
In addition to that I'm a self taught web developer. I started to teach myself about 4 years ago, and have been working nights and weekends as a freelance web developer for about two years.
I have been feeling burned out in the classroom, and have been looking to leverage my skills and my experience into a new career. I have been applying for jobs as a web developer, as well as jobs in the edtech sector. All in NYC.
I have applied for jobs that I am perfectly qualified for including web developer, curriculum developer (I've been writing my own curriculum for my entire career), staff trainer, technology teacher trainer, customer liaison for edtech companies helping schools begin using new technology, and countless others. I have gotten interviews, but never closed the deal. Some of these positions I was so qualified for that I was baffled that I didn't get the job, and completely unable to imagine what they were looking for.
I know that I am not a perfect human being, but the fact is I have always been personable, articulate, and completely comfortable in interviews. I am extremely comfortable with public speaking. I have gotten high scores on every standardized intelligence test I've ever taken. I have a bachelors in digital arts and a masters in childhood education so I have the credentials for these jobs. And again - over a decades worth of experience in the field. This shouldn't be that hard.
I should also note that for the past few months I have been writing a different cover letter for each job, customizing it to the job posting, as well as making changes in my resume for each job when appropriate.
I have done the following in order to attain a new position: -applied for jobs online (glassdoor, indeed, edsurge, etc.) -attended many meetups (often running into the same people and developing a rapport) -reached out to my personal network --I check linkedin whenever I apply and if I have a mutual connection at the company, I ask the connection to make an intro. -developed a solid and diverse web portfolio that utilizes all of the main front end web developer tools in use today -used slack for job searches (often this has been successful in netting me freelance work) -gone to a career counselor (admittedly only once, but I followed her advice - I just found her very flaky and she was difficult to get in touch with) -reached out to companies that weren't even hiring, but that inspired me, and told them to keep my resume on file -communicated with tech recruiters who have reached out to me (although they have been very inconsistent in a lot of ways and I don't have a lot of faith in them at this point). -other things I can't even remember at this point since I've been at this so long, but I'll update the post as it comes.
I should finally also note that whenever I have heard any communication back from job that I've applied for I always send 1 to 2 follow up emails if the don't get back to me, and whenever I have an interview I always send a thank you email within 24 hours and another one about a week or so later if I still haven't heard.
Exhausted, I gave myself a 6 week break from looking. Now I'm feeling the need to get focused again, and when I look at the trello board I have for actions I can take toward getting a job I feel overwhelmed, prematurely exhausted all over again, and frankly depressed. I don't understand how other people are doing this. My ex switched jobs like 3 times in the time that we were together (although admittedly she was working in the entry level of things - but I am qualified for the jobs that I'm applying for so that should count).
Please give any advice. I'm really struggling with morale and I don't know what else to do.
Thank you

Hey! You're not really special, as a huge number of people have been laid off over the past year and a half. This is mainly due to the fact that businesses began to lose profits during the coronavirus-related quarantine.
I recently finally managed to find a job using this site: Urgent! Journeyman electrician jobs in Newfoundland & Labrador - August 2021 (with Salaries!) - Jooble
Just take a look at this number of attractive vacancies! Plus, they are all pretty high paid.

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