I've been using Quicken for the past three years, and I really like it. I also used Microsoft Money briefly a few years ago. Both of them were easy to use, so I don't think learning the program will be an issue.
As far as accessing your bank and IRA online to do all the balancing, it pretty much depends on your bank, financial institution, etc. Different places offer different downloading options. Some places might charge a fee to download data to these programs. I would check the places you plan on downloading data from to see what formats they offer before choosing a program.
I also found
this comparison of the two programs that might be helpful.