Hi Grant. I definitely understand where you are at. Before I got my first deal done I felt like I never had enough information.
My advice to you would be to join your local REIA and network with the people there. They are not going to try to sell you anything and most of the time you can find people who are willing to give you quality advice and point you in the right direction.
For my contracts I actually worked with a real estate lawyer I met through my local REIA. He has done a few contracts for me and gave me a decent rate. All in I've spent about $300 and a lot of stuff I've asked for he hasn't charged me anything.
As for your second question you can do all of those things if you'd like, it depends on your strategy and your research. My first deal came from driving for dollars. I actually met a code enforcement manager with the city who sends me leads regularly and sometimes gets me in contact with the sellers.
You need to figure out your strategy, join your REIA and network and at some point you just have to quit researching and start doing, that's the hardest part... Once you start executing you start figuring out what you need to do and how to do it.