You can create a custom menu and assign it to the sidebar, let me know if you need any help with that task.
Maybe this tutorial will help you a little on the right way. Wordpress The Basics And Most Common Tasks

menu buttons or bubbles that go on the side of your web page

Mike I don't quite know what you mean by buttons bit there are menu options. What are you trying to make happen?

I think it is better to start earning from your website, and your own content first. I would only consider paying for your content from your profits.
You will, as IMc suggests, be better placed by researching the companies first however.

It depends. Better to learn to write your own content first. But if you want to produce multiple sites ; don't have time to write your own content or want someone who's a better writer than you to do it then outsourcing is worth doing.

But you'll need to research where to find good writers and also have an understanding of what good content looks like. Plus how much you should pay for it.

yes there are more pro's than con's certainly

If it is free I would give it a shot. Who knows you might hit a homerun.