A problem I have seen on several boats including my own, and particularly when mine used to be a charter boat is that the fore sail has not been hoisted high enough. It is important that the foresail halyard makes as broad an angle as possible between it and the forestay where the halyard meets the swivel. If the angle is too shallow there is a real risk of the halyard getting wrapped around the forestay making reefing difficult at best to impossible at worst. Using a winch can put too much strain on the furling line, and on my boat the charterers onboard at the time actually broke the furling line and that turned the situation into a near disaster
When hoisting the foresail, it is all to easy to shackle the tack of the sail to the furling mechanism and hoist the sail until it's tight. That is totally wrong.
What you need to do is to hoist the sail as high as it will go first in order to get the angle between the halyard and the forestay as broad as possible, then look at shackling the tack to the furling mechanism. If it's pretty much there and you are looking at needing to slacken the halyard just a few millimetres only, then it's okay to do so while you fit the shackle and then tighten the halyard again. If you need anything more than a few millimetres do not slacken the halyard, but firstly consider that your sail has either shrunk, or it was cut too small to start off. In this case use a small line some four to six mm diameter and take several turns through the tack of the sail and through the furling gear shackle and pull the turns up as tight as you can before tying the line in place.
If your fore sail is already up and you have had problems with furling it in the past, take a walk along the pontoon with your binoculars and have a good look at the angle between the halyard and the forestay. If it is more or less parallel or with only a very shallow angle, then most likely your furling problems have been because the halyard has wrapped around the forestay. If there is a lot of halyard reaching down to the top of the sail, then it's almost certain it will be at too shallow an angle and a halyard wrap will be the most likely cause of your furling problems.
Lastly, there's nothing wrong with turning your boat either head to wind or a slight angle when wanting to furl, and this will make life easier, as also will reefing before the wind gets too strong.