You can pop a tube in, inflate hard then deflate and hope one side will stay secured while you remove the tube from the other. That’s half your battle won and should make inflating tubeless easier.
Washing up liquid with a dash of water rubbed onto the bead and edge of the rim helps the bead slip into place and slightly obstructs the air escaping as you inflate.
I’d say do inflate with stans fluid in.
You can try to massage the bead of the tyre into the right place before inflating. I always do this, but am always well aware it moves back towards the centre of the rim as I work my way around.
If you have the valve at 6 o’clock you’ll blow lots of fluid out as you inflate. Messy.
I sometimes squeeze the wheel between a wall my leg and push down on the top. Sometimes this closes enough of the gaps to get the bead to slip into place. The help of a friend is even better for this one.
Check the valve is tight and the tapes looks good.
If using a track pump just take a deep breath and give it a good thrashing. I’ve never had a tyre I couldn’t inflate with a track pump.
You could try the homemade coke bottle compressor. Google it.
Good luck!