Not over 65, but have friends who are. Helped one of them get a cell phone, a Jitterbug.
Biggest issue I've run into with people older than me (I'm 53) is the belief that they are not able to understand the technology. Had an older friend who was put off by Tivo, but after some encouragement (and my printing out step-by-step illustrated instructions) she's now amused by the idea that she ever thought it was difficult.
I don't think things need to be dumbed down. The problems are not cognitive (for the most part; there certainly are older people with mental impairment, but I'd consider them a special case).
Older people are not dim, they're just from a different culture.
You have to address issues with vision and possibly motor coordination. (This is what makes the Jitterbug phone so nice. Big buttons, big text.)
Biggest use-case I see for the older people I know would be text chatting (maybe) or automatic phone conversation transcription (definitely).
Many have hearing loss, making phone conversations frustrating or impossible. I'm skeptical that older people (65, 70+) are going to get into texting or IRC (but I know of exceptions) so inexpensive high-quality voice-to-text would be a major win.
BTW, the age range typically defined for the term "boomer" is so large as to make it meaningless. There's a big different between 55 and 75. It's a marketing term I wish would die.