I dont think theres actually much work involved in going from SP14 to SP17, the main thing you need to be aware of is the attachments folder structure change, look for document itsm007474 for more info.
out of interest how come your only upgrading to SP17, why not move to a higher SP?
Also, try the upgrade in a development area, if you make errors its not a problem, just roll back the database and reattempt until you have success. another example of test, test and more tests!
Back up the database Image (ghost) the application servers
To roll out the client you can use the remote updater from the admin console (but have a back up in case it to not 100%). you can roll out the clients upgrade using SMS or Radia provided you get the current SMS or Radia package upgraded to SP 17 You can upgrade the clients by desk visits if you have a small number of them
Attachments - you have to run an attachments migration to the new attachments folder structure by running a perl script so you need to install perl and run the script before the upgrade and after the upgrade to catch any attachments in between
Test the upgrade Test the client roll out Test the attachments migration Test the rollback plans you have Test OVSD and any application that it intergrates with to ensure it all works e.g. OVO or a data import from a HR CRM application
Test it all in a test lab if you can so you can tease out the issues and reduce the risk in production