I'm hardly an expert. I've learned by doing, and I've just been doing for a long time. I still get twisted up sometimes. I once spent nearly an hour trying to figure out why I wasn't seeing an option that I knew should be there on a Vertex repeater, before I realized I hadn't set my new software to 'expert' mode. Rookie mistake, 20 years in.
If you never programmed radios before, Kenwood and Vertex are probably 2 of the easier commercial software programs to learn on. Kenwood keeps a very common software platform among most of their programs, so once you learn their software, you're pretty familiar with where to look for most any settings you might need to adjust.
For a first timer, I'd say that getting a basic codeplug set up for you from the start is a good jumping off point, and at least you have a working codeplug to refer to if you want to start modifying stuff on your own. Rule #1 if you start programming - SAVE YOUR ORIGINAL CODEPLUG before you do any modifications. Keep that original archive untouched, and you'll always have something to go back to.