I figured out what I was doing wrong on the first question. But the second question I still don't know what to do.
Make sure that all of your clips have the empty space removed. I'm pretty sure you that if you double click on the clip, it opens in the Edit view, just delete the empty space you've got, and when you look back in the Multitrack view, it should be gone.
Also, make sure that you've got your clips starting at the beginning of the timeline and not somewhere in the middle.
Additionally, you could always just select your clips in the multitrack view, and export the selection to get around that problem.
It depends on how much editing you want to do.
Click the "Zoom out Full Both Axes" button (top right corner of Editor, in the Zoom panel, or in the zoom controls embedded under the waveform if that is enabled.) and most extra space at the end of the session should be removed. The timeline always extends 10% beyond the end of the last clip in the session.