Learn API Technical Writing
JSON and XML for Writers

>How reasonable is it to expect familiarity with these things from an entry-level applicant?

As a technical writer, even one just out of school, you should be familiar with industry trends and some of the more common tools that companies are using. However, it wasn't the responsibility of your tech writing degree program to tell you or teach you about this kind of stuff. You need to be the one who is curious and looking around to see what's current and relevant.

If you're looking at job postings that mention these tools and you're not familiar enough with them to answer questions about them, then you need to start educating yourself. Hint: you'll be doing this the rest of your career, so get comfortable with this kind of mindset now.

You can learn DITA for free (https://learningdita.com/), and it shouldn't take you more than 30 minutes to learn the basics of Markdown, and then pick up any additional syntax as you go.

Tools like MadCap Flare and Adobe FrameMaker and RoboHelp have free trials and a ton of online resources available so that you can learn the basics.

There are also a number of online courses, for free or for not much money, that teach API documentation.

>Is it reasonable to expect a technical communication program to teach or provide an overview of these things?

To my mind: not really. Tech comm programs need to teach the foundations and fundamentals of technical writing, which are the same no matter what tools you're using.

There are always new tools to learn, so it doesn't make sense for a tech comm program to focus on making you an expert in any one tool. And as a tech writer you'll be expected to be able to pick up a new tool very quickly - it's just part of the job.

In your case, I'd start making a list of what's being asked for in job postings, and then look around to find resources to at least become familiar with those tools. As an entry-level hire you shouldn't be expected to be an expert, but you should be expected to at least be familiar with the basics, even if that means you learn the basics on your own.

Some thoughts...

It's never an easy cut and dried "do this and profit" thing with finding work. I average more than 200 CVs sent out to get an interview that leads somewhere. Persistence is VERY important.

1. Keep applying.
2. Refine the CV to highlight the skills he does have (after 30 years, he will or at least should have skills in demand).
3. Write a cover letter for each application - do NOT use a generic cover letter.
4. Note solutions/plans in the cover letter on how and when he is going to relocate - on his own vs expecting a relocation package. It's hard to get a relocation package with tech writing jobs in Canada/USA (compared to Europe/ME). Employers will typically expect you to deal with relocation yourself. Employers looking at his CV will see some overseas address and be concerned about his status in USA/Canada, his relocation plans, his availability. This needs to be addressed up front.
5. Be prepared with Skype, Zoom, Highfive, Teams, Jabber etc. Being he is in the ME, he will have to do video conferencing.
6. Don't limit to just Canada/USA... look at Europe too. There is demand for experienced native English speaking tech writers in Germany, Austria, Czech Rep, etc.

Technical skill set is a big part of the game. Employers love it if they can find a writer who already knows their product inside out, but that's typically only the staff they already have on the team, not new-to-the-job employees. That said, brushing up on things like APIs (at least on the terminology and lingo), and familiarity with a few bits and bobs surrounding the currently popular development platforms and tools will go a VERY long way towards potential employability. Some things to look into are (with Udemy course suggestions):

• Confluence (and MediaWiki) https://www.udemy.com/course/introduction-on-jira-and-confluence/
• Git https://www.udemy.com/course/git-with-bitbucket-and-sourcetree/
• Jira (see the link next to Confluence above)
• Python https://www.udemy.com/course/python-for-absolute-beginners-u/
• API https://www.udemy.com/course/api-documentation-1-json-and-xml/

This is NOT an exhaustive list, but... it's a start. If someone can speak the lingo and understand at least SOME of the conceptual things around the common tooling, they will be more interesting to a potential employer.

Next, and this is a VERY important one, is a portfolio of writing samples. Is there anything at all that he's done, that is published or publicly available (not under an NDA) and can be referenced as an attached PDF, a link to a website, etc.? if not then make something. Do some work for an open source project - LibreOffice is a good place to dive in and do some doc-writing - and use that as the writing sample. Otherwise, create something... create a writing sample showing a procedure, a descriptive text, and maybe a marketing text (doesn't have to be for a real product, it needs to show writing ability).

Finding a job to apply to is an art. LinkedIn is a strong place to start. Also look into Indeed https://ca.indeed.com/ for Canada and https://www.indeed.com/ for USA.

Edit: spelling