all those games are now almost 30 years old, they will need maintenance
Maintaining Star Trek is best left to someone with some experience
i would not buy x-files

I would buy one of the remaining games, pick the one that is in best condition, and is at the price range you are happy with

Don't let their age scare you away, all pins need maintenance, both old and new. Even brand new Stern/JJP often need fixes or adjustments directly after unboxing. As an example; new Sterns are infamous for having really crappy coil stops that often break and have to be replaced after only a few hundred plays so new games are no guarantee for problem free games.

If you intend to own any pins you need to learn at least some basic maintenance skills like soldering, tightening screws (need tools with inch sizes and not metric) and a digital multimeter for basic measuring.

That said, I find fixing pins equally fun to playing them, so the repair/maintenance part doesn't have to be a bad thing. It's very satisfying identifying and fixing a problem. If you can't find the problem cause then pinside and other places have a lot of knowledge and helpful people to ask.

Now to the games and this is only my personal opinion ofcourse:

* X-Files is a rather boring pin, I would not recommend it. I know my pin friends avoid it too.

* Star trek the next generation is considered a really good game by most pinheads but it's not a favorite of mine, most probably because I'm not that interested in the star trek universe at all (I find the movies rather silly and boring to be honest). This game has lots of stuff that can fail and can be a bit cumbersome to keep 100% working. Probably not a very good first pin unless you really love the theme.

* Theatre of magic and tales of the Arabian nights are very good games imo. Both games are pretty similar in theme/feeling (magic/mystic), both have captive balls, some similar ramps/habitrails, both have a magnet ramp diverter and mechanical outlane ball saves. I already own ToM and plan to buy ToTAN too when I can afford it.

Most neighbour's and non pin friends tend to go directly to my ToM and stay there when they come over. The theme is great, rules are easy to understand and the game is simply fabulous art wise. Also, I want to add that it's my wife's favorite pin and she have played 130+ different pins on locations over the years so that got to mean something. She even bought the official Pedretti topper for it for her own money

If you buy ToM try to order the "Indistructable trunk" mod from here on pinside. The normal trunk cracks fast from ball hits and have to be replaced pretty often while the indestructible one are more rubbery and will hold. I got one after changing trunks two times. Also get the trunk opto diverter in metal as the original plastic one almost always cracks and fails.

The only thing bad with ToM is that it's unbalanced score wise and the rules are pretty shallow so more experienced players may/will get tired of it. This isn't an issue for new or casual players though.

* judge dredd is a fun and underrated gem. It has lots of ramp/habitrail action, several flippers, drop targets and is generally just fun. The music soundtrack can be a negative thing for people not liking that kind of music but as a metal head it's fine to me

The eagle topper is cool imo but beware that it can be easily damaged at the claws if you fold the head down so be careful of that.

If you buy this game you should restore the deadworld multiball physical lock functionality as it's a really cool toy.

* I'm assuming you mean Bram stokers Dracula (BSD). This game is a weird one to me. Similar to STTNG this game have never "clicked" for me but I know many praise it. I think the game is rather slow and being a bit empty/boring but it's probably only me that haven't really understood it.

The mist multiball is probably the only thing I like about BSD but on the other hand, that feature is really awesome and I never get tired of seeing the ball floating across the playfield.

I won't mention the prices you listed simply because it's hard to know what's the right price without seeing lots of pictures, obviously overall condition is very important. Pin prices have increased a lot the last 5 years and they are expensive nowadays.

I suggest you ask the current owner/s to get to play the games for a bit (at least 30 mins each if possible) before deciding what you really like and what to buy. Everyone's taste is different and you might hate what I love and vice versa.

Best deals here in this market:
1. TOM at 8K: Best title in this lot.
2. TOTAN at 8K.

BSDrac at 3.3K is worth grabbing too.
Xfiles, Star Trek NG and Dredd just forget at those prices

Some of these are quite popular. Is theme important to you?

Star Trek is a fantastic theme integration. If you're not a fan, it might not be special for you. I personally love it more than anything on your list. ( I have owned one and had it restored). It is prone to break often. If you are lucky enough to meet Steve Ritchie at a pinball show and tell him you have that game in you collection, He will ask you "Does it work?"

ToM (8K) fully restored
ToTAN (8K) Fully restored
X-Files (3,5K) Fully restored
Drakula (3,3K) Working condition
Startrek NG (8K) Fully restored
Judge Dredd (4,5K) Working condition with topper, new cabin decals

Go 100% for TOTAN, it’s unique and amazing, especially the audio package is top notch, magnets, great ramp, butter smooth orbits, smash toy and so on, beautiful and a great game.

Out of that list I’d lean towards Star Trek first & JD second. Star Trek is a great game with some more depth than JD or BSD.

As others have mentioned, you must be prepared to learn repair skills as those older games will require maintenance. If you have no interest in repair I would recommend focusing on a new stern. I’ve owned several new sterns and they are far more reliable than the 90’s games at this point. With a new game your first several years are likely to only require basic cleaning and maybe simple adjustments or part replacements. It’s impossible to predict if or when a 30 yr old game may have a major failure.

TOM and TOTAN get old quickly. I would rather have Dracula and JD (2 games) over TOM or TOTAN. Xfiles is a fun flipper when it was $1250, but not at todays prices. STNG can be had for around $5k even in todays market.

imho, the best game among those choices is BSD. It is fun and challenging, and a relative bargain at $3300. TOM and TOTAN are good games, but for that money, I'd recommend a new Stern Premium (Godzilla?) Far less maintenance, lots to do.

You should snag a newer Stern. There are some goods titles there but the code depth and support of newer pins is outstanding. And at 8k there's not many you can't snag that are proven great titles. Unless you appreciate nostalgia I think the older games are a compliment to the newer vs where to start. Go new.

STTNG is one of my favorites games. I actually bought it twice cause i sold it and regretted it and bought another one.
That said, it is a very temperamental game. You need solid electronic experience to keep it running correctly.

When I bought my second one it was a hot mess. I had a switch column out on the CPU board and a coil out on the driver board. It’s rock solid now.