I appreciate your worries.
Well I just took the plunge (one hour ago!) after me and mrs running Crests / Bontrager tubeless ready rims (tubed) for the last couple of years.
Stans yellow tape, valve stems and goo.
My 29er Crest with new Purgatory tyre (quite tight) blew up easily with track pump and no goo. Just popped off one bead and put goo in then good to go.
Mrs’ 26er Purgatory and Bonty rim (quite slack) wouldn’t blow up dry with the track pump. Almost chickened out but decided to go for it with goo rolled around the tyre and some frantic pumping. And it worked first time!
We’ve had real problems getting tyres to seat tubed on these rims (multiple attempts with soapy water etc to try and get the bead to pop up to full diameter). Tubeless the beads popped into place much easier.
I’d say give it a go! (just watch the Stan’s videos)