tl;dr I think I'm being taken advantage of financially,

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tl;dr I think I'm being taken advantage of financially, what should I do?

>been working since I was 16, squirreling money away
>lent some money to a friend at university to help him with his project
>he started a company that later got bought out by a tech giant, earned me a nice amount of money
>still working full time

>don't really like people so don't have many friends
>spend a lot of time on the internet
>meet a girl and fall in love, buy her some stuff for her birthday a year later
>doesn't work out in the end, but remain friends
>seen her on cam so I'm not being catfished
>she says she's been stalked before so doesn't give out her details
>the guy she's currently with has her phone number as well as one of her internet friends, but I don't
>only way to contact her is via Skype
>talking less and less, has never initiated contact
>is having financial problems, her mum can't pay the phone bill in time and wants to borrow $250
>say I'll send it when I get to work, go to bed and wake up to 3 voicemails from her (goes through skype) to check whether I sent it
>even calls me at work to check whether I sent it
>we talk for a few hours when I get home and then she goes cold turkey again

>3 months later same thing happens, she needs $300
>keeps calling until I send it, then cold turkey

I know that I'm being taken advantage of here but due to the small amounts and the fact that I have money I don't really care. I realise though that it's unhealthy, so should I cut contact with her or say something before I do? I've left out a lot of details here but she's not really a gold digger as there are times when I've offered to pay/buy things and she's said no. I enjoy talking to her, but it seems she only really talks to me a lot when she needs money. Otherwise it's a few typed messages every other day or so