It is only very occasionally I hit any critical error. It has only happened when trying something obscure, like "Microsoft Maps for Excel".
I haven't tried Outlook 97 yet.
But poor old Access won't even get off the ground. I'm guessing due to some ODBC driver too stodgy to have a sip of Wine.
I actually used Word 97 to write a report for university. I switched Arial for Calibri and they were none the wiser.
This is speaking of IT of course; if you are talking to a small business doing woodworking or whatever, all bets are off on what tech they can and cannot handle. I'd still bet on PDF more than doc(x), though, since maybe they don't have an expensive Word license but PDF should render in browsers.
So, someone going out of their way to type their resume in wine word, only for it to be a scrambled mess... I would strongly recommend you not to do this. If you're emailing your resume and you absolutely want to go ahead with your plan, please consider adding both the pdf and docx. Good luck!
The idea to send it in both versions is actually very good. Thank you!
Then again I have (reasonably) positive memories of MS-Mail. The version of desktop Outlook I have to use (2016?) is a horrible buggy mess.