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Notes -
I know your post ties these questions together but I think they are actually pretty distinct.
For the first question, one of the best grounds to argue against compassion is its effectiveness. Pretty much no one wants homeless people to exist for their own sake. Even the "compassionate" side wishes there were no (or fewer) homeless people. The question is do compassionate means actually function to reduce the homeless population? Are we willing to devote the kind of resources that would be necessary for those means to succeed? As @guesswho says, we could just build every homeless person a house if we were willing to commit that level of resources. The best way to attack compassionate solutions is probably to argue against their effectiveness, either in total or in terms of tradeoffs. "This thing might be good to do but would not be worth it" is an argument everyone can understand (though perhaps disagree).
On the second question it depends on what you mean by "cruel." If you think we should merely leave the homeless alone, devoting no resources to helping them, I think that becomes a variation in the tradeoff argument I discussed above. On the other hand if you want to inflict some more active harm on them you are going to have problems. My impression is lots of people think some good reason is required to justify harming other people. Those people do not generally regard "does not have a permanent residence" as being a good reason. Often discussions about homelessness focus on other bad things homeless people often do as justification but is this other behavior that is functioning as justification, not homelessness itself.
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