Hey brother Paul,
A lot of people never go because they can't find someone to go with. While the written Word talks of the deciples being sent by two, and the Word also says that there is strength in numbers, there is also disadvantages by being with others. Often there is a tendency to lean on a partner when a difficult situation arises. This isn't any different than leaning on your own flesh, it won't work. It is God that will protect you until that time, not another man or woman.
Another advantage to being alone is that you are less threatening to those your among when you are by yourself. Some people, especially when they are by themselves are more likely to listen to you when you are by yourself. When you are walking in the power of God those places and people that are saturated with darkness are actually afraid of you. Jonah was one scary dude.
I think that people like Ray Comfort have an advantage by not being real tall too. A large person can be threatening to certain people. God uses peoples weaknesses instead of their strengths most of the time.
The early Church was persecuted in extreme ways and many Christians were murdered for their testimonies, yet the Church grew in leaps and bounds. Just think if there were half as many Christians who would walk in Moslem countries and speak the truth as there are Moslem extremist who are willing to blow themselves up and die for a false god.
It's all about death whether it is to the self life or actually being given over to the Lord to the place where one is willing to physically die for the Lord. Of course this death isn't just something that happened somewhere in the past. We need to die daily and be surrendered to his will with the peace of God in knowing that he is in control no matter how things appear.
It seems to me that having someone gifted in music to be with a speaker would work to draw attention of a crowd when the idea is to have the Word preached. Some people can do both. Some who go by themselves do one or the other.
I read that Wesley often went where ever there was already a crowd. Also, why does there have to be a crowd? Remember, Jesus goes for that one sheep. Praise God for the peaceful park bench with one lonely person sitting on it who the Lord is drawing. The main thing is to go.
So, whether God leads you to a bunch of knife carrying gang bangers, crazy motor cycle people, demonic looking people with tattoos all over their faces or that person on that little park bench, as long as it has been the Lord's direction to be there, it's in his hands and he'll do the work on them.
God bless you Paul.