Will you help a friend that is addicted to drugs and homeless with cash ?

No.

Addicts are brilliant at manipulating others into giving money. They lie, steal, sneak around, and deceive. They can't not because the drug is in control of their behaviour.

If this person has managed to survive her addiction for 20 years it means she's a master at survival. She has an encyclopedia of resources: places to find shelter, second hand clothes, food, and the means to hustle for money for her drug of choice.

I'm in CoDependents Anonymous. Codependency is what's called a "process addiction". One is addicted to helping addicts or people in serious forms of dependency.
Helping them helps patch the addict up after each crisis, thus enabling and prolonging the addiction.
Codependency is an amazingly destructive process. You appear kind, good and heroic. You feel you're being so wonderfully virtuous. But it involves trying to control another's behaviour. It drains your energy and resources till you yourself are in crisis, usually depressed, possibly to the point of suicide.

Others cannot help an addict; only an addict can help him or herself. Each person has a "rock bottom", a point at which being an addict becomes intolerable - it's different for each person. They will remain in denial (imagining they can control the addiction) until they reach that rock bottom. It could be some serious health or emotional crisis. But some never wake up to the truth. They die.

A 12-Step program involves coming to believe in a God or Higher Power who (which) can help get off the drug(s).
If the person is an atheist, the group can be treated as a higher power. (In CoDA, I chose Unconditional Love as my HP and find it works.)
The program involves choosing a sponsor, who has themself successfully recovered. They help by being available for phone calls and meeting - but it's tough love and nothing but.
Regular meetings, making amends for past transgressions, healing the wounds that caused the addiction in the first place - all slowly create a new and functional way of living. It's an extremely hard process because it involves first the withdrawals, and then accepting and facing all the pain and problems that the addiction once masked or medicated.
There is no easy way to recover.

Please do not let this addict con you into giving her money. The sooner she reaches her rock bottom, the greater her chance of recovery.

I would not give her money. The best help you can give is to care from a distance and pray for her that she will hit her rock bottom and get help. Harsh words, I know. But enabling an addict is the worst thing you can do for them.

I tried to help my nephew who was addicted to meth and living on the street. He wanted to busk, so i gave him a really good guitar and he gave it away for one drug hit. I let him come home to have a shower and have some food and he smashed up the place and refused to leave. I had to call the police to get him out and they dragged him away kicking and screaming. Sadly it was only when he was forced into rehab that he got off the drugs and got his life back. He's good now but nothing i did to help him worked.

That's such a difficult situation to be in. A close friend of my family was also stuck in this dilemma, and they did everything they could to save this person. What you can do is pay for the rehab instead of handing the cash to her. That's what they did. In return they would give this person an alternate incentive to look forward to that is also addictive (in their case, it was video games). You can discuss with the rehab facility as well what alternate addictions can help her wean off of crack. She might have to stay in the facility for some time.

If shes hungry give her a burrito instead of cash. Or a blanket. Or whatever. No cash.

I wouldn't do anything

That’s difficult , I would buy her food and things she needs but I wouldn’t send money, that’s what I did when I had friend who would take drugs to cope and because he hung out with people who did. We are still friends and he’s got a room in a flat two years ago and I’m hoping he’s making better decisions. I wouldn’t give up on her , addiction is an illness you can help her without giving her money. Hopefully if she realises One day she has a problem she might get the professional help she needs. I had a cousin who was in the same situation too but he died unfortunately of a drug overdose when I was 18 and my aunty would give him money all the time.

Don't send money. Maybe a voucher that can be used for food. It's awkward, but what can you do?

I'd help them find a rehab, food, water, shelter, but wont give cash.

NOOOOOOOOI will only help him check into a rehab

If they need help and tell me what would help them and I have the means or the ability to, you bet, they're going to get what they ask for.

Refer her to the National program targeted for addicts. AccessToRecovery
https://www.samhsa.gov/find-help/national-helpline

There are shelters and rehab groups to offer assistance with the addiction and homelessness, but the person would have to actively participate. And giving them money would only enable them in their addiction.

If you haven't seen her in five years, and she's come asking for money - I'm sorry....youre being used .

Drugs, although addictive, are a choice....ive been there.

If she had lost her home, friends, etc to this.....you can't fix them.
Helping is only a patch ....and shell come back for more.

You can help her find help , like rehab ....but only if she wants it.

Also.....keep your home security up.
Things coukd.....go missing if you get my drift.