Blog Summary Page

I am relatively new to WP. Know HTML, CSS & some php.
Theme: Sixteen
Site: http://woodenwineart.com/blog/
I want the main blog page to be the title, a thumbnail image if one, a sidebar with the categories, a summary of the post, cascading down the page with the most recent one first.

When I set the Blog page to Posts page (Reading settings), it has a not-so-great look. Squares with place for an image (not all posts will have images), no summary, no sidebar (that I have set up for the rest of the site) and the page title reading Recent Posts.

I know how to restyle most on the page, even the squares to some extent, but I am stumped how to the page be like I described in paragraph one.

Any help will be greatly appreciated. I have searched and searched for an answer. with no luck.