Yes, you may need a good pump..
I've done a few with the only problem being getting the bead to seal.
The new tubeless rims are much easier, so if you have tubeless ready hookless it should be quite easy.
This is using mtb tyres, so I'll say yes to road tires and CX, all about the air volume from the pump, you can use a car air line at a garrage or a new boost pump
Some tires like continental heve thin walls which can take a while to seal completely, but they will seal
the tyres have lasted the in-bound 30km to work without any dramas. 40psi in both feels quite smooth but takes a little time to get used to; it feels a bit like your regular tyre feels when it's got a slow puncture.
might put an extra 10psi in the back as i usually prefer a bit more air in the back wheel due to the panniers on the rack.