Like it's more messy and involved due to erasing and the like so I feel more pressure to get it rightYou need pen-rotation to emulate calligraphy properly, irl calligraphy brushes are elongated ink pens that look different as you rotate the pen. Keeping a fixed angle is ok for certain calligraphic writing styles but the angle is too forced for most art styles. If I recall only the Wacom Art Pen supporting tablets can handle true pen rotation.
You may get on better with a regular tablet, you may get on better with a screen tablet, even for longstanding pros it varies a lot and there's an expense to it. Most tablets are good/bad based on their technological accuracy rather than whether they have a screen or not, and surface texture is usually much better for non-screen tablets.
Unfortunately, iPad I don't think supports pen-rotation but you can probably emulate ink-brushes with the pen-tilt but in general I'd avoid calligraphy in artwork unless it's something you specifically are going for stylistically as it tends to make your lines look more fun than they are accurate which is bad visual feedback for a beginner.
Am not sure what you mean here. What do you mean by physical or harder here?