He keeps making the same mistake, because he doesn’t know better.
This is a criticism of himself, and it may ultimately be a reference to the crime that got himself into the situation in the first place.

He has became comfortable in his fear of the law.
He feels like the fear keeps him safe, as it spawns caution from the law, and helps him cope with being isolated from the rest of the world.
He feels like this ‘fear’ is almost a friend, as the fear is a constant companion.

He doesn’t think that he has a chance reasoning with the law, and he believes them to be so convicted on his guilt that he has no chance talking to them.
This is why he’s running, because he doesn’t see himself as having a chance for a reasonable fate any other way.

To be ‘wanted, dead or alive’ is for the police to be able to bring you back at all cost.

This means that they can do anything, as long as they have a body to bring back, thus ‘dead or alive’, as he can be captured alive, or killed.

This signifies a severity of the crime, as it is apparently punishable by death.

The saying ‘wanted dead or alive’ comes from the Old West period, where the law would put up posters for criminals that are wanted, for bounty hunters to pursue and collect on.
The posters would say ‘Wanted: dead’ or ‘Wanted: alive’, depending on the severity of the offense, and Foster claims the crime to be severe enough to call for a ‘dead or alive warrant.