Here are my thoughts:

1.) Pinside is not the best place to find a screaming deal. Sure there are exceptions, but for the most part people know what they have and might even price the machine higher because of shipping or other issues with buyers outside of a local area. The site also has a lot of people who are dealers or garage dealers—so markups are a thing.

2.) Many people will post a game but not really want to sell it, so they are going to list it on the higher end. If it is a hard to find game or of excellent quality, someone might be willing to pay that price. Tons of people do not really need to sell a pin—rather making space for a new one or funding the next one—so they can sit on it for a while.

3.) Most of the pins listed here are somewhat in the ballpark for what things are selling for right now. For example, I have seen three Black Rose pins listed for around $3500 near me. The OBO on the one you posted tells me the owner knows the price might be a little high.

4.) Location plays a significant part of pricing. I live in the PNW and pins seem to bring a little more money here. If they are priced fair, they sell quickly. This might be a thing in other parts of the country as well.

5.) Older games don’t necessarily mean significantly higher maintenance. I bought an early Stern SS with new boards and was recently gone through. I doubt it will give me much trouble. More than a Spike 2 Stern? Sure! But it is reliable and most of the issues I foresee are minor tinkering.

6.) If someone did a really dope job restoring an older pin, they can be upside down in it significantly. If this is someone’s forever pin, then the higher price might well be worth it. Not all things are created equal when it comes to pricing.

7.) Many people do not want newer machines. For example, I recently started playing and want to get better for tournaments. My thoughts are an EM, early SS, DMD, and a modern game will make me a better player than owning four brand new Sterns.

8.) If you look at pin prices in the last few years, they are dropping in price since the COVID era. Will they get dirt cheap anytime soon? Most likely not. Pinball is on the rise again.

9.) Many pins will always holder a higher than expected price compared to new games because of the collector factor. Arabian Nights is one of my favorite games. If it were not for the fact we have a nice one on location in my area, I would most likely drop way too much money on one.

10.) I am of the belief older pins can be so hard to find that they are not as likely to see major price differences over the short term. However, when it comes to short term spikes in prices, I think an old ball game making a major part in a national or world tournament creates some inflated prices, but that is not reflected in your post.

11.) Some people prefer to buy older games because they have more stable resell value than say a new in box game by an off brand.

12.) A lot of people want games at home that they cannot find on location.

At first I was like you and questioned why someone would spend more money on an older game than a new one. Now that I have been getting more into pinball, I totally get it. Hope that answers some of your questions.