yehudah

Add a meta box to all posts, pages, custom post types to add the old url you want to redirect from (old url) to the new post. 
You can use redirection plugin here: <a href="https://wordpress.org/plugins/redirection/" rel="ugc">Redirection Plugin.</a> OR The other option is the website htaccess file.
This will help you create redirects while creating or updating your site posts or pages, so you don’t need to update the old and new links when you finish updating your website.
so you don’t need to remember:
<ul>
<li>The new posts or pages url</li>
<li>which post or page I all ready redirected ?</li>
<li>repeat 50% of the process again and so on ….</li>
</ul>

Redirect To WP

This will help you sync redirects while creating or updating your site posts or pages, This will sync to the redirection plugin or htaccess.

M.Code

Jan Fabry

Understand how rewrite rules work could be userful. 
Natively on WordPress you can’t analyze what’s working / not working regarding your urls. 
Through this interface you will be able to analyze every single url and see what’s matching.
Warning 
This tool will not change / add any rules for you it’s only an analyzer
<h4>Main features:</h4>
<ul>
<li>Live URL Analyzer</li>
<li>Highlight parameters</li>
<li>AJAX Permalinks refresh button</li>
<li>Change UI (Light / Dark)</li>
</ul>

Url Rewrite Analyzer

See clearly and understand how WordPress rewrite rules work within a simple and clean interface

Redirect To WP vs Url Rewrite Analyzer