Run with a Rapier scout and people will struggle to catch you.
Scout the next system with the Rapier. If it looks safe jump the Obelisk in, click warp to out gate. As soon as you can, target the Obelisk with the Rapier and put 2-3 webs on it. The Obelisk will warp instantly. Warp the rapier to the out gate. Because of the slow warp speed of the Obelisk, the Rapier will likely get there before the Obelisk. Jump the Rapier in an scout the next system. Repeat until you arrive at your destination.
Make sure the Freighter pilot and Rapier pilot is in the same corp or CONCORDOKEN will ensue.
It is quite possible to use a T1 Frigate or any other ship for this as well, but the Rapier has the advantage of extended web range. It should be something reasonably small and fast though.
In high sec you should watch out for battleship gangs. A bunch of Tempests sitting on a gate should certainly set your alarm bells of.
If you want to run through low or null sec I would suggest more scouts and a dedicated webber. Run a scout through ahead of time to check the overall activity. If it looks safe, use scouts a few systems ahead and behind the Freighter, making sure to check any side systems as well if necessary.
You could also set up a heavy escort of BS and logistics or something of that nature and hope you can overpower whoever wants to gank your freighter. I would opt for the scout/web approach personally.