Social Bookmarking - Software vs. Manual Submission

Hello Fellow Warriors,

I wanted to get opinions on how to properly do social bookmarking.

Background:

I want to begin social bookmarking my youtube videos and a few articles from my website for linkbuilding purposes. The website is my primary blog and has my best content. So I do not want to get penalized by google for suspious backling practices.

I have been compiling a list of social bookmarking websites that I want to submit my links to. I have been creating accounts to high PR sites manually. It is somewhat time consuming and will take me awhile to complete even the account creations.

Questions:

Is there a software that will automate the bookmarking process without being penalized or should I just keep manually creating these accounts and submitting my pages?

Does each bookmark title need to be unique?
Does each bookmark description need to be unique?

Is there a software that can do 65% - 75% of the account creation and unique title and description process?
What are some things I should be concerned about when using software?

I understand that I need to build links slowly and increase over time is there a software to vary bookmarking daily or weekly

Also, This will just be a part of my backlinking strategy, I will be including varied backlinking source. I am going to be first testing it on my youtube videos first the secondary blogs.