Is it possible to integrate JotForm with cloud services such as Dropbox?

Can Jot form do all this and more? what about file uploads? to say dropbox?

What plan would I need?

Yes, we have integrations with Dropbox, Google Drive and Box, here are the guides to integrate your form with these 3rd party services: 

Upload-to-Dropbox-with-JotForm

How-to-Integrate-a-Form-with-Google-Drive

How-to-Integrate-your-Form-to-Box

Do note that although you have integrated the form with a 3rd party service, files will be uploaded to your JotForm account as well, it means that the available space for your account will be used, here you will need to delete some submissions in order to get deleted those uploaded files, or you may upgrade to a paid account with the needed available upload space, in our pricing page are the details per account: https://www.jotform.com/pricing