After upgrade, front page only shows oldest post

Hello everyone!

I just upgraded from 1.5 -> 2.5.1. Previously I had a page titled ‘What’s New’. The blog’s front page contained my most recent posts. If the user clicked the ‘What’s New’ header, (after say, clicking on a few other pages so they couldn’t see the most recent posts anymore) they would be taken back to these recent posts.

Now that I have upgraded this does not work anymore. The front page still contains all the latest posts. But, when a user clicks on ‘What’s New’ now, only my oldest post is displayed.

I have deactivated all plugins and reverted to the classic theme, so I don’t think plugins or themes are my problem.

Under Settings -> Reading, I have specified the following:

Front Page Displays:
(checked) Your latest posts
(unchecked) A static page (see below)
Front Page: Overview
Posts Page: What’s New

If I elect to check ‘static page (see below)’ I start to get confused. If I make both the front and posts pages equal I get warnings and weird behavior. Why? Why can’t your front page also be the page where your posts show up? If instead I make the front page equal to Overview (as shown above) then visitors won’t be able to see the most recent posts until they click on What’s New.

Check out my blog at https://roguelikefiction.com to see what I mean.

Cheers!
Nathan