Yeah you definitely want to chat with Pale-Axe multiple times throughout your journey its actually super important for unlocking some really good content. Each time you bump into him especially around Woods of Ember and Furnace Valley, make sure to run through all his dialogue options cause theres usually something new to learn. Found this out the hard way myself when I almost missed the whole Bishui Cave area cause I didnt talk to him enough, and trust me you dont want to skip that content

The whole Five Element Carts stuff is particularly important so whenever he mentions anything about those carts, pay extra attention cause itll help you progress that storyline. Something I learned is that after big story moments, its worth checking back with him cause he usually has new things to say about whats going on. The conversations around Furnace Valley, and Field of Fire are especially important for triggering that Rusty-Gold Cart boss fight which is pretty epic

Just keep talking to him until he starts repeating himself, thats usually a good sign youve gotten everything you can from that conversation. Also while youre chatting with him, keep an eye out for any hints about the area youre in cause he tends to drop some useful info about hidden stuff nearby. And dont worry about bothering him too much - you cant really overdo it with the conversations, but you can definitely miss out by not talking enough. If you notice some dialogue options are locked just progress the main story a bit and come back, usually opens up new stuff to talk about