John's tips for off-the-wind furling are spot on - it's madness to try to come upwind in offshore conditions. But, off the wind furling is mechanically harder - the sail will be loaded. To be successful, you will need to optimize your furling systems.
Traditional Main Slab Reefing
The main enemy of main reefing is friction, the sail needs to drop down easily. If you struggle to drop your main on a nice day when heading upwind, off-the-wind reefing will be hard. This is a common problem, mainsail slides can jam in the slot, and battens can lever and get stuck. Your touchstone is to lower the friction enough to have the main drop (at least ½ to ¾ of the way) when you release the halyard when travelling upwind – when you reach this state, off-the-wind reefing will be a lot easier.