When I had a Fish Tales, I found kids were really drawn to it, especially girls. But those were visitors, not sure about longevity.

In order of fun for me it'd be BSD, SoF, SS, Monopoly and Gladiators.

It terms of reliability, Monopoly, Gladiators, BSD, SS/SoF.

If I were picking one as a first game to get my feet wet and wanted both a fun and more reliable game probably Monopoly from that bunch. BSD is the best player but the mist mechanism and the long range opto could be troublesome. But that would be my next choice.

Location?

jurassic park is great for a family and in your price range. My kids loved JP.

Not sure BSD is a great one for kids.

Gladiators is great imo, sof is fun but got old, monopoly is fun and kid friendly too

Welcome to your newest addiction. These things are like potato chips:

You can't have just one.

And I second the Jurassic Park comment. If you can find one for $2500, snatch it up quick. Great beginner game.

Love me some BSD but I would not recommend it for children under 12, or for a first pin.

Taxi fits into your price range. My whole family really liked that one and Fish Tales.

I feel like I see these threads a lot.

Is that a good thing or a bad thing?

Good thing. It means more people are looking to pay good money for our beat up old machines.

I'll second a Taxi like game. (Diner?)
Kid friendly, and decent ball times.

I here BSD can be a quick game, so maybe not great for kids?

Gladiators! Gladiators! Gladiators!

I wouldn't be looking at $2500 machines to get my feet wet. Lots of fun games between $1000 and $1500. Space Shuttle can be found found cheap and last in a collection.
Watch out..pinball machines multiply like Gremlins.
-Mike

Space Station is a great title. If its in good shape, worth all of $1500. If its not in good shape, buy something else to get started. Coincidently, Space Station was my first. I've had many many since (including owning Space Station more than once). Good luck!

I'm going with The Getaway.....

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I still think there is good value in those $2,500 DMDs. Just looking over the top-100: The Shadow, Bram Stoker's Dracula, The Getaway, Fish Tales, Road Show, Judge Dredd, World Cup Soccer, Jurassic Park, Terminator 2, Johnny Mnemonic, etc. all seem like you might be able to find them in that range. But there really are great games in all price ranges, so my suggestion is to make several lists and see what turns up in your area.

My kids loved the DW I had and is in your $2500 price range. In the list above I really like JD, WCS, and JP. I am unfamiliar with the titles you listed other than BSD and Monopoly. I honestly don't get the popularity of BSD and Monopoly is really fast. Monopoly, might not be the best kids pin.

Monopoly has a unique layout with a lot of toys. I like playing it on location, but it doesn't get the adrenaline pumping like Bram Stoker's Dracula (BSD). The appeal to BSD is that you're almost always a few shots away from a great game. Games are fairly quick, so you can keep hitting the start button and savor the moments when you start hearing Dracula saying, "10 million!", "20 million!!", "30 million!!!". I've owned many of the games I listed. Of those, Jurassic Park was the one played most often by friends. It has a good theme and one of the best toys in pinball. Despite that, I sold it off and brought in a Fish Tales. Another one of those games where you're always a few shots away from a great game. I actually like it more then BSD, but I'm probably in the minority there. I just really enjoy those crossing ramp shots. Seriously though, the best way to decide what you want is to play games. Personally, I like quick and simple games.

Judge Dredd, World Cup Soccer and Taxi are real bargains considering what they have to offer. They have been keeping my interest for years.

Since this decision sounds like it's based on the children....

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Get a Comet & save some cash for the next pin

Or if you really want a DMD pin, go Fish Tales or JP. Kids love those themes. Welcome to the hobby

PIN*BOT stranded!

This is probably the route I'd go, unless we really need DMD graphics. Taxi offers more than meets the eye. Plays fast. Kids will get good at timing shots like the ramps and the lock on the right side and Drac on the left. Easy, fun-to-shoot ramps that can light the million-point shot, and that always feels good. Two-ball multi won't be overwhelming and is a good for them to learn how to trap up and maintain control with more than one ball in play. Spinout skillshot has always been one of my favorites, and it's a good way to teach the physics of nudging as there is no immediate threat of drain for nudging it the wrong way. Worst it can do is stop spinning and drops onto the PF. Nudging a ball around a whirlpool can really help in other games like CFTBL or White Water.

Mark Ritchie had a way of making deceptively challenging, yet universally accessible games with simple, straightforward rules. Fish Tales is another good example, though one in the condition you want will probably be on the high end of your budget.