I do it all the time with $500 Visa/MC/Amex gift cards since I can get them with my Amex BCP at the grocery store and net 5.2% after fees.

I paid my property taxes online with in three payments on three VGC.
I pay my car and home insurance with Geico online (and previously Progressive) with two or more.
Costco will auto drain VGCs, so I will use up small value cards there and then a final swipe with a real Visa. Think the max I have done is three swipes.
I was buying something at Bass Pro Shops that was about $250 at the same time there was an Amex offer for $20 back on $100 at Walmart or Target. Target sold $50 Bass Pro gift cards, so I bought five. Cashier told me the POS would allow up to eight swipes. If enough swipes were not allowed I could have probably bought bigger gift cards with the small ones, then the merchandise in a separate transaction, but that might anger some cashiers.
I'm getting roofing and siding quotes now. One place agreed to waive their 3% CC surcharge, but I probably won't push it and give them 30 VGCs.