While it s based on v12 and shows Montoya's servers, it is still a good guide to understanding how to set up the on-line portion.
link
http://www.ootpdevelopments.com/boar...s-ftp-etc.html
So obviously having a website is key, since that is where all the files that are shared (imports/exports, etc are stored.)
The Commissioner panel will automate most of your work. Not the fastest method but certainly workable.
The league setup is the same as a normal league. That means you and your friends can setup whatever type you like. So you can practice your setup there, save it as a template and then create the on-line league.
Try and get a routine for how you sim. That will make mistakes less likely.
For example,
1) Pull imports from teams.
2) check for valid rosters (invalid rosters stop the sim so check before you start)
3) check status of players on DFA (this list shows if any player coming off the DFA list). If someone is coming off this sim it will stop the sim when it occurs, may as well do it early.
4) Process any trades.
5) run the sim.
6) export the results.
The order may vary by commish, but have an order.