She doesn't go out to eat all the time. It's rare occasions when we are in a group setting with 6+ people. We split the bill and offer to pick up her portion. Everyone pitches in, it's not just my SO paying for her.

She doesn't like it when we pay for her, but we're all friends and want her to come with us and enjoy a Friday evening. She works hard, she's not someone who expects others to pay for her.

Her SO also has a chronic health condition. I'm sure he does pay for her, it's just that he doesn't usually go out with us when he is feeling in pain.

I agree her situation is not in desperate need. She could rent her own place, but it would cost ~$500 per month more to rent from someone who she doesn't know. We would simply helping her save some of her hard-earned money. I think her new job's salary may be slightly below average earning income in this area, so that's why she can't afford to rent from a 3rd party at regular rates.

Now if it wasn't for me moving in with my SO, I'd say this scenario would be a win-win for her and my SO. He'd get a little rent income, and she'd have an affordable place to stay. I am being biased here because it took me so long to be able to move in with him and I do want to try living with him for a few months on our own to see how we get along living together as a couple. He is going to have a lot of changes in his work schedule and school schedule. I'm going to be looking for a new job. So on top of all these changes, having an extra roommate would make it difficult for me to see if my SO and I have problems living together. It might even make small issues worse because we might feel awkward talking it out with someone else living with us.

I'm trying to be fair. She's a good friend, but not my best friend. I want to give her the benefit of the doubt. There are no underlying schemes going on here.