So it looks like as long as I can get this .htaccess file to play nice, my answer may be "yes"?
Yes, and No. .htaccess isn't really what makes it work. .htaccess tells the server what to do once it does work.
The answer to this question:
will this be easy to configure once the site is live?
...pretty permalinks will only work if your server meets the requirements specifically mentioned for using pretty permalinks, in the documentation I pointed you to. So, if your web server meets the requirements, pretty permalinks will be a snap.
You'd think it would be easier to get some pretty permalink structure going. It feels like the Wild West days of WordPress design when things like this happen
The thing is, it's a server setup and configuration issue. Not really a WordPress issue. You must have a web server configuration that supports using pretty permalinks.
The good news is, it actually is quite easy to use. If mod_rewrite is functioning properly, (which it probably will be, once you purchase hosting from a reputable company using a linux server environment) the only thing really you need to do is to make sure permissions on .htaccess are writable to WordPress when you make the changes. Then when you update permalinks from the dashboard, the changes will be made automatically in the .htaccess file. Once you are done making the changes, you simply return the permissions on the .htaccess file back to the secure settings, and you're done.