Hey Thunderbird. I don't own a POTC (considering buying one) but do have a Dialed In and have watched a ton of the JJP live stream videos. I would say get whatever game you like the best, play both and get a good number of games in on each before pulling the trigger. As NIB games continue to become higher in price I would expect to take a greater hit on the secondary market. There's only so many pinball dollars to go around and I've found that selling newer higher end games takes longer then selling higher end Bally / Williams titles or Stern pro games. What drew me to Dialed In is how rich everything is in the game in terms of the animations, rules, sounds, music, etc.
Dialed In has a ton of toys with 5 magnets, the drones, theater toy, moving mechanic, large physical ball lock, moving QED toy, etc. Pirates has a lot of toys as well and I would have given it the edge over Dialed In in that department if the original 3 disk toy and moving chest was still in the game. After the production changes to Pirates I would give Dialed In the edge in toys. Dialed In offers a greater variety of toys and mechanical features then Pirates in my opinion.
I prefer games with deep objective based rulesets and both Dialed In and Pirates offer that. Pirates has way more modes then Dialed In but I don't find them to be as unique or as rich compared to Dialed In's disaster modes as all 125 chapter modes in Pirates play the same as there's no licensed actor audio / video from the films feature in any of them (other then a quick 2 second clip at the beginning). Same goes for each movie multiball in Pirates. There's a multiball for each movie but I don't feel like I'm playing through an event in 1 of the 5 films as there's no licensed actor audio / video. However, the 5 wizard modes in Pirates come across as very unique and remind be of the multi stage WOZ, Hobbit, and LOTR type mid wizard modes that I enjoy. Also, the pick of pirate feature in Pirates is super cool and combined with the map awards feature opens up a ton of strategy options. I can see the pirate character feature being a big draw at home for family, friend, pinball league nights, and tournaments. With the pick a pirate feature the lack of licensed actor audio / video in the game kinda fades away as you are then trying to maximize how modes are played in regards to scoring and getting through them quickly to get to wizard modes.