The cashback debit I use doesn't cap out at $25, but rather gives me $0.25 cashback for transactions over $25. So if I make a bunch of $25 payments it's essentially 1% cashback on credit card payments but it's utility decreases with higher amounts. Some pitfalls:
1. Tons of payments is vaguely suspicious to one or both parties involved (debit or credit issuer)
2. It's a lot of hassle...1% cb (untaxed) vs about 0.5% via interest (taxed) to just leave the money in a fidelity/discover/SoFi etc account at near 5% apy in current environment until the autopay takes it.
There's a few other recent problems too. Last week PayPal seems to have broken billpay to credit card issuers. Unclear if they are killing it or this is some temporary issue. My Chase, USAA, AOD are gone from saved billers and can't be found in the search, my remaining cards no longer work to pay by debit... although I haven't tried deleting/readding them.
Also I haven't tested this but I vaguely recall the Citi SYW management site saying somewhere you were limited to 5 payments a month? Couldn't find it just now and probably only applies to website payments and not phone calls but don't know for sure.
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