Do not attempt to use Windows Live ID. It won't work no matter what you do. Ignore "recommended". Either have a conventional password or no password.
From most banks, the best you can do is to download an OFX or QFX file from the bank's website. There are exceptions.
Many US brokers and credit cards can have PocketSense download transactions to Money. It is not as simple to set up as you might hope, but it works very well for most of us who use it.
If you want a better supported product consider Quicken. I like Microsoft Money, but it takes some more effort to get things set up.