3) How do I change the font for headers? I'd like something a bit more compact width wise, not necessarily heighth wise.
There are a few different ways to change the heading above each post or page.
The first way is to modify the CSS and use a web-standard font - that is a font that a user is likely to have already installed, which will allow them to view the heading as you intended.
For example, something like this:
font-family: "Arial Narrow", "Helvetica Narrow", Arial, Helvetica, sans-serif;
A visitor would need to have one of those fonts installed on their machine. If they didn't have the first one, the browser would look for the second in the list, and so on.
Here's resource with some common web-safe fonts:
An easy way to add custom CSS like this is to and activate Jetpack's Custom CSS module, since you're already using Jetpack. You'll then add any custom CSS in a special CSS editor, under Appearance > Edit CSS. This way, your CSS won't be overwritten when you update the theme.
Here are some helpful resources for learning about how to customize your CSS: