Even with the valve core removed the initial rush of air is often not enough to get the tyre to bulge enough that it captures the rest of the air to seat. Sometimes frantically pumping can aid. That is if the pump doesn’t come loose from the valve
I havent take a valve core out in like 5 years except to put sealant in or replace them 
I actually leave the valve core in for that, a lot less messy
Santa Cruz / Reserve Fillmore valves, get across it!
It doesn’t matter how much air/pressure you put into your current valve, it’s enough of a restriction to prevent the CFM you need to flow in there.
Add another layer of tape or two to the rim. It takes some of the gap under the bead that lets air escape.
Are these Comti Tires? I’ve notices they’ve gotten slacker in the bead new and seem to get worse on remount
That’s one option.
Or, a floor pump designed for tubeless…
Topeak and some others have similar designs.
I would only get a compressor if you think you’ll use it for home projects.
I already own these
The only floor pumps with the canister I could find were twice the cost of the Airshot, and I already have a floor pump that works fine. 
Ah, didn’t see you mention what pump you’re using.
I’d try the Fillmore valves or some other high-flow valve and see if that helps.
I need special valves from Vittoria because I want the Vittoria airliner insert