1. You can submit each leg as it is or submit all the legs in one go when you've completed the tour......it's entirely up to you.....but remember each leg has to be reported on a different flight report
2. No you cannot submit the flight. What the OPs manual probably meant is that you can use the planes to fly around for things like exploration of the FS world but if it's not a scheduled flight in the timetable it cannot be reported. However there may be exceptions with online training etc.....not too clear about this last point
3. The award request page can be accessed from your pilot profile. Just log in to your profile and look at the service menu and click on the link to 'request award'
If there's anything else you need to know feel free to ask!

(please correct any mistakes i've made in this reply

)