You can certainly start with a good qualiity non- digital scale. I used one for years, and treated properly they never wear out. Digital speeds things up, but I have never found they are more accurate. Calipers are essential for checking case lengths. which stretch after each shot. Especially for semi auto rounds, this is crucial.
I would start with the .38/.357 round. It is a strait wall case which is very easy and forgiving to reload, not to mention that the cases are cheaper than rifle rounds for the inevitable screw ups while adjusting the dies.
The cleaner your cases are when sizing and reloading, the more consistent and easier your loading quality will be. There are inexpensive washes you can use which work fine, but a tumbler is easier when you can afford one: just be sure to clean the cases, regardless. I have many hunting friends, but none of them load anylonger. You can certainly self teach, just follow and stick to the safety guidelines: you also are less liikely to pick up the teachers bad habits.