Fonts and Copyright Issues???

Okay, so I have heard that using a font or an illustration (that was not designed by yourself) in a logo design can lead to copyright issues.

Based on this knowledge, I have been going around in circles trying to find answers but have not had any luck. I have come across a few websites but they too, do not really explain that well - or may be it's just me. So I thought, why not blog and ask and see if someone can answer my question.

I will use the following scenario and try to keep it really simple. Say, I am a freelance designer and have been approached by a company who wants me to create a logo for them.

Using Adobe Illustrator, I create a logo using an illustration I designed (freehand) with a pen tablet. Then I use the default font - Times New Roman font and type the title. I create outlines of the font and export as JPEG and then sell that JPEG to the company.

Here are my questions (I apologize in advance if they are too confusing):

1. Can I legally (in Canada), sell this JPEG file to the company?

2. If not, why?

3. Do I have to "buy" the copyrights for using Times New Roman font??

4. If so, how do I do that? Also, if I am buying the "copyrights", would I bill the customer?

5. Could you provide all the steps that I should/need to take to ensure the logo I design is legal and is sold in a legal manner?

These are only some of the questions I have. I am hoping I can find some answers as this issue is really confusing!

Thank you all in advance!!!