I'll chime in here - as others have said its totally personal preference. I play a minimum of 2 times a week plus at least two range sessions and I re-grip once a year. I use GP multi-compounds and I find that the rubber portion under the thumb of my right hand wears fastest and is a good gauge when its time for new grips. I also use either dish soap or Fantastic and a small scrub brush to keep them tacky.
For your 1st attempt I'd recommend getting the "kit" with the individual tape strips to get you started.
I graduated to using a small air compressor and I can pretty much remove any grip intact except Iomic's (they never come in 1 piece). If you want to go this route in the future there are tons of good videos on YouTube.
Good Luck!

I believe the industry guideline is every 60 rounds. For me its about once a season until this year. If I keep practicing and playing at my current rate, I will need to redo my grips at the end of May. Thankfully I love re-gripping my clubs.