I’ll be honest, I’ve never had a valve I couldn’t remove, but did have a couple of occasions when first running tubeless where I was swapping tyres end-to-end and the lock ring was reluctant to let go, needing pliers to get enough grip. That prompted me to check valve cores and lock rings more often to avoid any roadside Basil Fawlty moments. To actually pull/push the valve through just wiggle it around to break the seal and then twist from the base. I tend to use valves with a rectangular base so that helps. If you’re pulling a valve at the road/trail-side remember to remove the core first, then you can use a twig or other non-marking object to push against the end of the valve stem.
How often you check sealant levels and top up largely depends on the sealant used. Stans is notorious for drying out well before the stated 6 month lifespan. Whereas Orange Sealant, Magic Milk and some of the others really are good for 6-9 months before needing a top up. I stopped using Stans years ago because it was quite high maintenance. Magic Milk and Orange Sealant have been much better. Finish Line have just announced a new sealant that never dries out. Time will tell on that one.
As for maintenance (top ups and cleaning etc) I set a calendar reminder for 5-6 months to check levels and then look to swap tyres front-to-back at around 9-12 months depending on mileage and wear rate. Thirty mins with some hot soapy water and gentle scrubbing with an old (softened) bit of scotchbrite lifts most residue out and cleans up the bead enough to form a new seal when you mount the tyre. Just don’t scrub too hard on the bead as you don’t want to expose any threads. Same process for the rim-hook, but use less water as you want to avoid lifting the rim tape, and to dry as you go with the rim. Plastic tyre levers with a decent hook profile are good for forcing the scotchbrite into the rim-hook to clean ‘em out thoroughly.
Important: don’t go too crazy cleaning out the carcass as you’ll unseal any perforations that the sealant plugged for you in the last year’s riding. This’ll make it much more work to get a seal when you refit and re-fill the tyres.
So essentially, you’re looking at 10 mins work every 5-6 months to check levels and then maybe an hour every 9-12 months to swap tyres round and refit/refill. Plus a couple of mins every month or so to check valve cores and lock rings are free and to give ‘em a quick scrub if needed. Granted, it’s more maintenance than running tubes but I’m pretty certain I save far more time in fixing flats at the roadside, and the ride comfort and handling are drastically improved.