Mountain biking tubed is dumb.
Gravel riding tubed is not advised.
Road riding tubed is fine.
I spent the first 30 years riding mtn bikes with tubes. It wasn't dumb then. It is now. Tubeless really is a huge advantage for mountain bikes and gravel bikes. If you don't think you need to go tubeless on the gravel, you're probably riding places you could ride a road bike.
For road bikes... yeah, that goes both ways. I ride tubed and tubeless road bikes. I don't get many (jinx in 3... 2... ) flats with the tubed bikes. I went tubeless because of a set of wheels that are brutally hard to mount any tire. I've grown to like the tubeless road setup. Yes it's more of a hassle. Yes, you're much less likely to flat.
A compressor usually works fine (yes, removing the valve core) for road tires. For mtb tires, I use a magic inflator (Bontrager Flash Charger). If you're struggling to seat the tires, try one of the inflator/pumps made for the task. They really are effective.