Smooth rounded boxes in Illustrator and path end angles

Question

I'm new to Illustrator but have a decent background in Photoshop and After Effects. Anyway, I've spent a good amount of time creating this logo in Illustrator and am unhappy with the results. It's likely that I've used the tools incorrectly.

Here are my list of questions:

1. The rounded corners don't seem to connect to the straight lines in a smooth fashion. How would I clean that up? Is this caused by the fact that I used a path/stroke? Should I have taken a different approach?

2. I cut angled corners off the "B" on a rasterized layer in Photoshop. How would I make sharp angled ends on a path in Illustrator?

3. Is there a way to approach creating a design like this that will auto-magically make the outer wider rounded corners have a wider radius? Or is this something I'd have to do manually? I really dislike how dirty it is a the moment.

Here's the image as reference:

Thanks for reading, I look forward to your answers.

Answer 1

1) I am having a hard time understanding what you mean in question one. What do you mean they don't connect smoothly? Can you circle the area that you're talking about?

If you think this is a stroke issue, you can always expand the stroke. Select the object and go to object - expand and make sure stroke is checked.

2) You can use a clipping mask. Create an object with the pen tool. Fill it with white and place over the logo.

Select both the logo and the new object.

Open the transparency panel and select "Make" (In the image below the word "Release" is where "Make" would be) and the select "clip"

The result:

3) You can use path offset.

Create your object with round edges. Select the object. Go to object - path - offset path and put desired offset.

Result:

You can then use the Direct Selection Tool to move the points hover you like.