Nik - Good for you for thinking strategically about the finances. If you can just "happen" to end up with a little extra cash in your wallet left over from grocery shopping or whatever, all the better.
The contact with OW may not be exactly what you think - often these idiots have a hard time cutting that cord even after they've "come home" - but I agree with OT that you have to set some clear boundaries on this now, it's been going on way too long. As soon as you get your financials in oder.