What places are best for a first tatto in your opinion?

Pain to me is not really that important a metric. Figure out where you think it'll bring you the most joy. Most of mine are reasonably visible and I'm very glad for it. Tattoos are much less stigmatized than before.

As for durability, as long as you take good care of it while it heals and you wear sun screen after, most places other than hands and feet will likely do well. Less sun the better but that makes them hard to look at most of the time.