I've got a classic game I want to share with those who may not have had the pleasure of encountering it.
This is an old roguelike that was sold commercially in two parts using the shareware business model with the first one being available for free. There are still a few physical boxed copies out there for sale but fortunately both parts of this game have since been released into the public domain by their author and are now freeware.
The game is called Castle of the Winds.
► Physical Game Box: Castle of the Winds I - A Question of Vengeance.png
► Physical Game Box: Castle of the Winds II - Lifthransir's Bane
This is a graphical tile based roguelike that ran on the Windows 3.1 OS which may make it much more approachable than some of the other ASCII art roguelikes you may have seen.
Like many roguelike dungeon crawlers the goal is to get to the bottom of a multi-floor labyrinth without being killed by the inhabitants. Although not as complicated as some other games in the genre it does feature a decent number of spells and enchanted equipment to find along with a rather easy to understand user interface.
During character creation along with configuring your stats to your liking you can setup the game to use a custom player tile if the game's default blue underwear clad barbarians are not your style.
And if I'm remembering correctly once you get to the end of the first game you can import your character into the second one and continue the quest.
I'm not sure if you will be able to run either of these games directly on a modern version of windows but there are two methods that should allow both games to function. Either configure
DOSBox with a copy of Windows 3.1 or setup
Wine and it should be able to handle the Windows 3.1 software.
Here are the files for both the first and second game.
Castle of the Winds I: A Question of Vengeance
https://f.rpghq.org/L9jhovo8gEkr.zip?n=castle1.zip (Size: 412.81 KB)
Castle of the Winds II: Lifthransir's Bane
https://f.rpghq.org/jTHwJo89BGco.zip?n=castle2.zip (Size: 357.98 KB)