I don't know if you mean boomer in the 2021 sense of the word, which is like, just anyone over 30 - or, in the actual sense of the word, like people born in the 1940s - 1960s. However, I have to say that 'my boomer dad', who was born in 1947, gives me much the same advice. LOL =)
'Squeaky wheel gets the grease, son."
Must have heard that a million times, and it holds true to this day. Sometimes you gotta be the squeaky wheel. It's not ideal... but it is what it is. I worked text- and voice-based tech support for many years, both as a front-line or "tier 1" agent, and as higher tier II and tier III support. There are indeed things that simply won't get done unless you insist to go over the 'tier I' agent's head.
I don't say this to disparage SE or any tech support in general... I just offer it up because this is the way a major ISP handled their tech support, and I witnessed it first-hand. 'Front line' agents are meant to be a triage unit. Granted, they should be escalating matters they can't or won't help with, but if that ain't happening, sometimes you have to get "creative". /shrug
Good luck OP.