Your question had How to run, so I assumed that you want to have a solution to your problem.
It's good that you want to contribute, you need to be open to all possibilities of learning. It is not copying it is actually a solution to your problem number 4, once solved you can try...
If you may re-read my comment you will find this line You can try to install CyberPanel and then replicate your configurations to your setup.
I already know that you want to do things manually, which is why I specifically wrote this line so you can replicate settings. You just had...
You listed out so many questions but lets first jump to question number 4.
I suppose it is relatively easy to set up document root outside /usr/local/lsws. This is what CyberPanel actually does. You can try to install CyberPanel and then replicate your configurations to your setup...
Cache module is loaded in OpenLiteSpeed, but it won't work until you send specific cache-control headers that it looks for. I am not sure how you have coded your application, but did you look at the documentation to setup Django on DigitalOcean https://docs.litespeedtech.com/Cloud/django/
Aaron, there is a slight difference of rules with OpenLitespeed, you need to add forward slash.
For more details : http://open.litespeedtech.com/mediawiki/index.php/Help:Rewrite_Rule_Differences
And if we take example from one of your rule it should be something like