Hi there,
I'm glad to hear that you are thinking about transferring from Tumblr to WordPress.com here :) I provide the answers to your questions below. Please let me know if you have further questions.
1. I don't know how WordPress's pricing works. I have a custom domain that I have paid for till Sep 2018. How do I move to WordPress's custom domain service? What is the pricing for it?
→If you have the custom domain already, you can map it to your WordPress.com site. But you need to upgrade to the Personal Plan in order to perform the domain mapping. Please refer to this page about the paid plans for WordPress.com.
2. I don't know much about web hosting. I'm assuming Tumblr was free hosting so I didn't have to pay anything, but how does it work for WordPress? Is web hosting included in WordPress paid plans? If not, what is the best and most affordable solution to set up WordPress website hosting?
→WordPress.com provides free web hosting for all plans. You don't need to worry about it.
3. I have a couple of articles on my blog which have a couple of backlinks. How do I move those pages from Tumblr to WordPress and add a 301 re-direct to them to the new pages in WordPress?
→This helps you to import the contents from Tumblr(Import »Import from Tumblr : https://en.support.wordpress.com/import/import-from-tumblr/)
4. What is the WordPress desktop app for?
→Here is the page you can download the desktop app of WordPress.com. https://apps.wordpress.com/desktop/
5. When I try to install a plugin to my WordPress free account, it downloads the plugin (as a Zip file) on my desktop? How do I use that download to install a plugin on my wordpress site?
→Any plugin installations are not allowed on WordPress.com due to the security reasons. Please refer to the following support page about plugins.Plugins : https://en.support.wordpress.com/plugins/
Source:
Moving my blog from Tumblr to WordPress
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