1. How does the upgrade work? Will I lose the money?
No, you will not lose the money when you upgrade. It will be prorated i.e. remaining time on the current subscription is reduced in duration to match the new subscription amount. The days will be adjusted accordingly when you upgrade to a higher plan.
2. I am on a free trial and want to upgrade to a higher plan. Will I still get the remaining free trial days?
Yes, you will still get the free trial of the first subscription however the remaining free trial days will be prorated based on the price of the new plan.