I started off reloading with a Hornady LnL AP loading 9mm, ironically to help feed my Hipoint back before I had an LTC. Using an auto-indexing progressive press is probably less dangerous than a non-autoindexing press due to a lesser chance of a double powder charge, especially if you fully complete the ram stroke. In that case, it's no more dangerous, certainly much less challenging, and more expedient than reloading for rifle cartridges. You're going to wish you had gone progressive much sooner once you start cranking out those rounds!
With either major flavor you choose, Hornady or Dillon, there are TONS of sources out there to help you set up and troubleshoot whatever issue you may come across in the beginning. It honestly is not that complicated or difficult, just need to pay attention and take your time, just like anything else mechanical. I know you're more than capable!