Is it likely not a good idea to BP to the same card you have linked online or load your Serve account with?

I'm MSing my CSP (online) and Club Carlson (in store), and nothing else right now, as I'm building point balances for a specific trip and those are what I need. For February, I just withdrew it ACH into my bank account, but I don't know if that's a best practice routinely, plus it was <$2K because I started late in Feb. I added my fiancee as a payee (different name and address) and can cut her checks, but I don't know about doing that with large amounts. I don't charge nearly as much as I MS in actual spend on my Citi/Chase cards, either. Maybe just split it up a bit?