Michael

If you're more about goals than points, the Paradox Interactive-developed grand strategy games would be up your alley. They're all very deep and based on the same engine, but each game has its own "theme". Europa Universalis III is probably the most well-rounded and most-liked Paradox game. It's an overall country simulator that takes place from 1400(?) to 1800ish. While the game gives you intermediate goals (send ships to the new world, annex so and so), the goals of the game are completely up to you. Taking over the entire world isn't very feasible but you can choose to, say, conquer the entire Iberian peninsula. Note that if you go with EUIII you want "Chronicles", not "Complete". Complete is not complete as more expansions came out after it was created. The other games have their own themes. Victoria II is a victorian-age game that's mainly concerned with its simulation of the world economy. Hearts of Iron III is a WWII simulation. Crusader Kings II is a dynasty simulator in which the interpersonal relationships of your heirs and various court members are the main point of the game. Lots of scheming. Sengoku is the only one I don't have, but it's been described as being closer to CKII. Personally Victoria has always been my favorite, but it's something of the red-headed step child in the series. In any of the games, you should warm up to the notion that sometimes you don't need to be doing anything, and letting some time pass is the best way to progress.

I enjoy Brogue quite a bit. It's a very accessible, very well-made roguelike with some great touches added to the standard ASCII interface. Rather than bogging the player down with classes and skills right away it allows them to progress naturally as their play style and item pickups evolve what they're good at. It's a great alternative to some of the more beastly roguelikes. My personal favorites are Dungeon Crawl: Stone Soup (which has both a console and tiles version, free as in speech and beer), and Dungeons of Dredmor (graphics only, so cheap it might as well be free). Of course, there are also the Big Roguelikes such as Nethack, Unnethack, and the Angband variants. DC:SS is the one that really grabbed me. I could go on about Roguelikes... maybe we need a thread for that. Brogue was a great suggestion, and I just wanted to expand on it and let people know that there's a lot out there!

I would definitely start with Reamde, then. It's very Stepehenson-esque while still being his most accessible book. I just finished it and really enjoyed it. It's more of a straight up thriller than a genre book. edit: To elaborate, I thought it had great pacing and memorable characters. My heart lies with the Baroque Cycle, as those are my absolute favorite Stephenson works. I've read almost everything he's written, and feel like Reamde is the best place to start, followed by Cryptonomicon. Then, if one were still so inclined to continue with the author, Snow Crash and then the Baroque Cycle. I actually didn't care for Anathem.

I'm just getting started with OOTP myself, and I found these videos to be pretty helpful. If you're interested in seeing how the game plays, you can jump through these and get a feeling for what you might be getting into.

Have you registered over at the Paradox forums? Once you enter your game key (so they know you bought the game), you have access to the tech support forum. I've gotten some great help from Paradox employees there in the past.