Hi Jerms, I wanted to pop in this thread and give a bit of context.
You are working with a DB coach and I understand that the advice given by the coach was to help your W feel "safe and comfortable" with you.
In doing so, I know you question that advice in so much as you think you are enabling your W.
At the end of the day, if you do not want to follow the advice of the DB coach, that is completely your choice. And I mean that to validate if you feel you are enabling your W and do not want to, then do what works... FOR YOU...
You will get support in what ever you choose. Although I will submit that there is very likely ways to keep your W close to you and "safe and comfortable" with you, in ways that will not feel you are enabling her.
Try to figure out why you feel you are enabling her by following the advice of the DB coach. Look at those specific points rather than justifying that your W isn't working or looking for work, so you will simply stop giving her money until she finds a job, as though that will be some incentive to get her to find a job.