I own a handful of pins, and I feel a couple of them are quite difficult compared to other pins of their era. But there are 2 kinds of difficult. There is the annoying difficult, where you just get frustrated, and the game doesn't make you a better player.
Then there is the good kind of difficult, where with practice you can get better, and your skills clearly get better. Also, the "good difficult" keeps you coming back for more, gets you addicted, makes you determined to beat the pin, nail all the modes (on modern pins) or beat a high score.
2 of the pins I own that I think are a "good" difficult, from 2 different era's, are Spy Hunter (early SS) and Judge Dredd (90's
DMD era). Both pins are tough at first, but they really improve your skills, gradually, and you do get better.
And I'm not talking about the
VP versions, as those tend to be a lot easier for me, for example the flipper gaps are smaller.
With Spy Hunter, everybody who plays that for the 1st time has pretty quick games, even with 5 ball. If you want a pin to work on your nudging skills, SH is definitely a good one, between its mini flipperless PF and brutal outlane area, good nudging is a must to get high scores. There is also a pretty large flipper gap and some rewarding but risky shots.
JD, what an underrated modern pin, a supergame option, deadworld mod, 1st Bally to use DCS sound.
Want a challenge, JD will offer it. I have a super clean JD with a 7 degree incline. Fast & furious. If you play a pin like Paragon for a while, where you can have a cup of tea as you play, then move onto JD, it will murder you!
JD has no letup. No bumpers to slow down gameplay, no video modes (well, there is kind of a video mode but the ball is in play during it). Even when you get the ball in the subway, the ball will start to shoot out to the left flipper almost immediately. Only time you get a break in play is when you lock a ball (obviously), or hit the air raid ramp (which is one f**king bastard of a shot, but I'm getting better at it).
Then, 6 ball multiball is just pure chaos.
I set my grandma up on JD over the holidays. LOL! Instant drain! She didn't even have the reaction time to see the ball come down the PF after it is launched! I showed her what was happening, but she just didn't have the reaction time.
So, JD, not great for grandma. Not great for kids (& some of the audio/video is a little adult themed anyhow). But for true pinheadz, its a great pin. And JD might have a couple of the fastest loop shots around. For the large loop, you need great timing/reaction. For the small loop, even I still don't have the reaction time to keep nailing that one.
JD is important to keep finely tuned. Keep it well leveled, keep the PF clean & waxed, get a nice slope on it, have strong flippers. Take care of it, and it will kick your ass.
The important thing here though, is that I keep getting a little better at JD. And that is exactly what I want in a pin. Something that I can't master right away, yet also something where I don't get bored because my ball times are like 5 minutes. Many modern
DMD games I've played, as I get better at pinball, just seem too easy for me to want to own for a year (which is generally what I do).
I think part of the reason I've taken a liking to early SS pins about as old as I am is because they are fun but hard. My EBD, Flash, & Spy Hunter all keep providing some level of challenge. My EM is sometimes challenging, sometimes not, kinda hit or miss.
Though I admit, on all these pins I keep the PF's clean & waxed, good strong flippers, and steep slope. Playing these same pins, not maintained, can make a pretty big difference on difficulty.
Point is, whatever you get, if the stuff I mentioned above is well taken care of, you can turn an average difficulty pin into a tougher playing one.
Anyhow, I can name so many older pins that are very challenging.
DMD pins, many can be challenging as far as completing all modes or whatever, but easy as far as longer ball times & such.
& that is another aspect of pin difficulty. Do you want something that challenges you with short ball times? Or something that may have longer ball times, but harder to reach goals?
JD is actually good with both of those things, short ball times, and a buttload of modes to beat.