My favorite is the funeral home commercials on oldies stations. It basically says, "You're going to die soon. Don't be a burden on your family."
Some of the "music of my youth" I listen to near every day. (Some of it I don't ever want to hear again. I expect it's that way for most "old people".) But the kinds of ads you refer to (including from funeral homes and such) are about as welcome as having to hear ads for Clearasil or Giacobazzi Wine. (Extra credit if anyone can identify who did the VO's on Giacobazzi when it first started advertising.) OTOH, if Pepsi or Schaefer Beer (for example) resurrected those classic 1960's radio ads to advertise their current products, that would really grab my attention. It's not resistance to ads, it's revulsion at the way the ads are constructed, written, what talent is cast, and clustered together into those damn 10 minute audio brick walls.
Most "old" people are not stupid. They (we) have learned a few things since we were diving for cover during those 1950's air raid drills. And the advertisers and ad industry doesn't win brownie points by insulting our intelligence.
Some seniors may have money but most are brand loyal and reluctant to change. To give you an idea, I operate a YouTube channel aimed at cutting the cord with an antenna. What takes for some seniors to invest a measly $200 in a good antenna setup while they willingly pay thousands of dollars a year for cable shows how reluctant they are to change. They'd partially or completely eliminate their monthly cable bill but they don't like the concept of change so many just stick with cable/satellite to watch the price is right.
Plus, IF an advertiser could convince them to purchase their product, they'd probably only have them as a buyer for a decade before they pass. An advertiser may get 4 or 5 times the business if the target someone younger as they will live longer.
I might not be the best person to respond to this -- I have an engineering degree, a computing/IT specialty and a First Phone (which, if I also have $3, will get me on the subway next time I'm back in NY), and four TV's in my house with four discrete OTA antennas -- but you are misidentifying your problem. It is not only "reluctance to change". OTA TV is largely garbage these days, programming-wise. A lot of sports is on the cable. Fox News Channel, CNN and MSNBC are on the cable. As is most business news (CNBC, Bloomberg, FBC, etc.), women's lifestyle (the Food Network, HGTV, Lifetime and a number of other "women-leaning" programming services), and children's channels for the grandkids, Comedy Central isn't available OTA. I could probably go on for another 200 words.
OTA reception is free, but you get what you pay for. Plus, you're on the hook to support it (or pay someone else to). With cable or satellite, the support is bundled into your monthly payment. And for some older adults who have retired to 55+ communities, the cable is bundled into their monthly/quarterly common fees, so there's no financial incentive to cutting the cord since you'll still be paying for it. The only actual incentive is having an OTA antenna an a backup for the [/sarcasm on] very rare outages of the increasingly reliable cable system [/off].
One other thing: add up the costs of subscribing to a few streaming services: Netflix $15.50/mo, HBOMax $15, Amazon Prime $139/yr, Hulu, Paramount, Disney, Peacock, etc. It doesn't take too many of those for the monthly tab to add up. Plus, the more that a household streams, the more bandwidth they need in their internet connection to avoid repeated buffering. So there is no free lunch, and unless you're willing to settle for the lowest common denominator of crappy network game/competition/talent shows, ancient reruns on secondary subchannels, syndicated dreck and local Stupid News, there's not a ton of quality programming for cord cutters. (Though PBS is there, as are Stephen/JimmyF/JimmyK/Seth/James. Their shows are often interesting, if you can tolerate 20 minutes a night of ads and 12 weeks a year of reruns. So it's not a complete vast wasteland. [hat tip to Newton Minnow])
I think I might have wandered a bit off topic. Sorry.