Someone on this newsgroup suggested negotiating with my bank (CitizensBank, MA) for free transaction download service. I spoke to a branch manager who said they charge everybody $3.95 per month, even their "Gold" customers.
However, she said she would be interested to know if I found a bank in the area that offers the service for free. If I find one, she said she would bubble it up to management because they want to maintain parity with their peers. In the Boston area she mentioned Sovereign Bank, Bank of America, etc. but not any credit unions. I use a credit union as well but they don't do tranaction downloads to Quicken.
So it looks like banks like you to keep your money in their facilities and they will provide free web-based "bill pay" but they don't want you to use Quicken for issuing checks. They fail to appreciate the ability to categorize checks and to use one interface to handle multiple banks.