@JewelryNest - From where you are going to upload images ? I have sign up and see in my account as a customer there is no option to upload image at front side so.
For second question - as you are using paypal express checkout - so from cart page it will directly goes to paypal payment screen as its a there option.
still elaborate more on the issue so it helps us to troubleshoot more.
if issue solved,Click Kudos & Accept as Solution