I have a
Wacom Bamboo FUN (CTE-450) which I've had for almost a decade straight and I've never had to replace it or it's pen. I use it nearly weekly and sometimes use it entirely in place of a mouse at all.
My preferred art program is
Paint Tool SAI. It's simple but it has just the right amount of features for me. It costs ~$45 to get a license right now (though there are less legal means of obtaining it, of course). Free alternatives that I hear are pretty good are
FireAlpaca and
Medibang Paint Pro. Sometimes I still use
Paint.NET (also free) for basic functionality if I'm in a hurry, though.