Phil is definitely exaggerating the impact, either willfully or because he spends everything, ends up with a negative balance, panics and just assumes it's worse than it actually is.
I believe it was in November Phil claimed that the chargebacks totaled $2000 and negated everything OverPoweredBoone had given him in cheers that month. When it was pointed out that Boone gave him $3000 in cheers, Phil said 'it was the majority', and then the following week said he had another $1000 in chargebacks, conveniently balancing with Boone. In December, I think Phil indicated it had been upwards of $5000 in chargebacks since September. Anytime Phil is rapidly manipulating numbers, those numbers are conveniently matching visible income, or he is saying definite numbers at all, it's safe to assume he is probably making them up. I can't think of a time where we found he wasn't.
If SH's records of chargebacks are even mostly complete, Phil's total is also not correct - there is no way there were even $1500 worth of believable tips on there that Phil could justifiably have fallen for. But Phil is probably playing some semantics like calling every tip he had to refund 'a chargeback', regardless of if he contested it, lost it or immediately caught it. We've seen him bend reality with his pigmath.
I don't think he is directly colluding with SH, and I think SH has stressed him or cost him some money, but Phil's low cunning and twisting of the truth has actually resulted in the presence of SH netting him money overall. He uses chargebacks to pity beg when tips slow, he used it as a reason to disable notification to suppress troll messages and hide his money as he ramped up begging, and he has used the chargebacks overall to obscure the issue of the vest streak money apparently doing nothing to help him when he has no debt.
Phil probably would have been struggling harder right now if he didn't have SuperHound to hide behind. He's a far more useful boogeyman than restreamers.