My mom still uses OTA. I ordered a couple of coupons last March, waited a few months for them to arrive, then had to pre-order a convertor box from Sears because no one had the boxes in stock in the Chicago-city area. I checked Radio Shack, Bestbuy, Sears, and Target before I gave up. The original arrival date of 3 weeks was pushed back an additional two weeks.
When I went and hooked the boxes up, my mom said she had seen the commercials but didn't really believe them. She doesn't use the internet and couldn't check the websites, and it seemed like they were trying to sell her something. She still doesn't use the converters because CBS which gets a weak signal through analog, won't come through at all digitally. This is with a quality amplified antenna. I guess I can try a different type of antenna to see if that helps. She also gets confused with multiple remote controls.
To summarize, if I had left this up to my mom, she'd be stuck. She's not stupid, just not technically inclined.... she originally was an accountant. I'm hoping that more converter boxes are in stock now, but previously it took way too long to get them. Even with me buying and setting them up myself, she still isn't using them, and will need a new antenna and a universal remote capable of controlling the converter box before this makes sense to her.