This is a great thread. I've been having the same issues too.
My biggest issue was tooooo many usernames/passwords for websites, hosting, social networks, email accounts, etc. etc. I just installed LastPass a few days ago and so far so good. I like that I can use it on multiple computers and browsers. I still like having a backup like a spreadsheet and have been thinking about setting up an Access database for everything.
I'm a big OneNote fan and use it for research, to organize thoughts, and can setup tasks directly to Outlook. It syncs between all my computers via a syncing program I have. Interesting that a few people on this thread prefer Evernote over OneNote. I'm familiar with Evernote (may even have an account) but never really used it. I may give it a chance per these recommendations.
For project management I use
ClockingIT. It's free and a powerful project management system. It will help with your checklist. You can use it for outsourcing too because you can give limited access to people and will send reminders for tasks that are due.
I've been hurting in the time management area. It's too easy to get distracted with things online not to mention everyday life. So, I am going to use Rescue Time which is a very good time management program and they have a free version which should be good enough for most lone operators. If you do a lot of outsourcing get the paid version.
To help with the time management, I've been looking at various task list programs. This thread gave some great options, a few i wasn't familiar with and plan to check them out.