Best combination of plugins to use

I'm working on putting my first multi-site together. I have a feature set that I'm hoping isn't too complex for my first go.
User can:
- Post text, photos, and video updates from phone
- automatically optimize photos, upload videos to youtube and embed code.
- Simple way to add advertisements
- Use subdomain or their own domain
- Use API that will display information based on values the user enters
- Allow user to sell their own merchandise
Any feedback is appreciated, thanks!