Reduce Spacing

You can reduce the spacing between widgets like this:

.widget {
    margin: 0 0 30px;
}

Adjust the 30px to whatever you like.

As for making it inline with your featured image - that really depends on the height of your title/post meta area.

@media (min-width: 769px) {
    .inside-right-sidebar {
        padding-top: 28px;
    }
}

Excellent Tom!

Thank you!

You're welcome :)