So couple weeks ago, my technology illiterate mother asked be for help getting her a portable music player. As it turns out she found her old ipod shuffle but had frustrations with it. She had taken a liking to the DAP that I use and was even willing to spring for the price of one. I pointed her in the direction of some solid budget DAPs. Fast forward to today, it arrives and I get volunteered to migrate her small library over to red leather clad Hiby R2. Feels good to spreed the word of hifi. not so much the feeling of family IT. How about the rest of the community, what about your experiences gently introducing people into the hobby?
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I got my mother a pair of airpods pro. Simple and easy enough to use. Still see her using the wired buds that apple includes in their kit. She only uses the pros at night to help her sleep with the anc.
Before this, I gave my parents the Sansa Clip back in the day. Miss that little thing.
My mum and dad once bought me a Deep Purple album…I was 13 at the time 
since she seems to like her new DAP for Xmas she may get an expensive set of CDs to rip and put on it.