Who should the local congregation be evangelising?

I have heard that someone recently preached on how the church should be doing outreach to people whose alcohol addiction leads them to drink on the streets, people who are homeless and people who are sustainably addicted to drugs. Well I admit those are challenging areas to do outreach in. It is like it is a bit of a challenge to take the gospel to groups of people who no one has tried to take the gospel before. There are challenges and I fully accept its worth doing but...

... as someone who has been vaguely involved with it can I say there is one big problem, the area is over subscribed with those who want to be involved in it!  The people who around here fall into those categories go from one Christian mission to the next Christian mission and get food, clothing, worship etc from that.

The real challenge, the biggie, the one I fail at is ...

To take the gospel to people who outwardly are the same as us. To cross the taboo line in society and talk about the faith with your friends. To be prepared to be ridiculed amongst those you socialise with. To be prepared to adapt church so those people who have never been to church feel welcomed and treated with respect, because they believe they won't be. The challenge is not to bring the very different to Christ but the almost like us to Christ, who can and will ask awkward questions, may think you a religious freak and suspect you of judging them even if you don't.