You found the issue here with your question. They have similar content, so Google is showing only one. I would try to change the on-page SEO attributes of your articles to target different keywords.

It's not very often that Google is going to show the same site for the same search unless the articles are quite unique. They strive for diversity in their links.

You may be able to accomplish a little more uniqueness by changing the Title, H1, name of the article, subheadings, content, incoming links, etc.

I'm really really hoping to get out there. Still up in the air depending on how projects are progressing in house. It would be a perfect time for for some deep SEO knowledge as we'll be doing a site launch shortly thereafter.

If so, I'll probably have a lot of orange and black on (company colors)

It will direct the link juice from the redirected URL to your page, as long as you use a 301 (permanently moved) redirect. This will pass 90-99% of link juice from the linking URL.

To squeeze out everything you can get (pardon the pun) ideally you want a direct link, but a redirect will pass most of your juice along in the case you would have to get people to change hundreds / thousands of links.

Keep in mind here that just because you use a 301 redirect to point to your new page you won't lose the opportunity for your new page to rank. A 301 redirect will pass 95% of the link juice from the redirected page, which is great. Your new page will most likely rank once it starts getting links to it through people finding it through the old redirect and your site getting re-crawled.

301s are a great tool to keep in your SEO utility belt. Don't rely on them, but always use them when you need to move something.

If we look at a site like a human would, which is what search engines are evolving to do, then always matching exactly your Title and H1 tags is going to be pretty silly in my opinion.

Good practice is to use a few targeted keywords in the Title tag that describe your page well and the content within up to 70 characters. Of course not all pages will use the full 70 characters. That might cause stuffing penalties.

For H1 you might match some of what you list in the Title, but not exactly. You're going to have commas, pipe characters, other kinds of descriptions, brands, etc. Matching all of this would be crazy and would make a site appear very spammy.

Since the search engines are striving to be more and more human every day a good long term strategy is to build sites for humans first, and search engines a close second.