Literally everything is easier if you have a door you can lock and a roof over your head. Even if it doesn’t get you all the way.

I think if people “want help on their terms”, social/outreach programs should be designed to actually be appealing to those people and less restrictive, where possible. This might include stuff like, for example, allowing homeless folks to bring their dog with them into shelters, or just trying not to impose unnecessarily on their lives and autonomy (beyond what’s needed for safety of others) and not making help conditional where it doesn’t need to be (e.g. you can have a roof only if you get off this drug and take a weekly drug test, else you get the boot and can sleep in the snow again), because that’ll just feel like bullying/coersion and make them want to listen even less. Everybody’s more likely to do a thing if it’s an ask or an offer, and not a demand with an " or else" threat attached.