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System Free
Cartographer's Guild - People making maps with Campaign Cartographer then putting their hard work on the web for your use. High quality, name-checked in Penny Arcade no less and deservedly so.
EpicWords is a campaign forum/wiki/inventory set-up similar to Obsidian Portal. While there is a paid user option, you aren't reading this to hear about it. Simple, effective and low-key; it has no specific programming language requirements.
Gozzy's Dungeon Map Generator - One of my perennial bugbears is the provision of maps for dungeons (I used to be able to lovingly hand-craft maps...) so finding a map generator of this kind of quality makes me very happy; and the output is high quality which makes me happier.
HP Lovecraft Historical Society offer a number of fonts eminently suited to the manufacture of props for Call of Cthulhu (or it's cheaper relative Nemesis) which you may find suitable; some very nice blackletter fonts for those Gothic horror games you keep hearing about too...
RPTools - Java applications to help you roleplay at a distance. Dice, tokens, maps, characters and initiative trackers. All OS agnostic, you can network and game to your heart's content on installation; check the community for FAQs, tips and tricks.
System Specific
For 4E, there appears to be a quietly active community of people outputting free stuff for you to download (some of it in PDF - take note Wizards!) which can enhance your game.
Asmor.com - Why haven't Wizards hired him yet? Seriously??
DragonAvenue offers a selection of character sheets and power cards.
PlayWrite - Has the magnificent CrawlNotes and the 4E Power Toolkit to let you homebrew your own 4E stuff. Here's a thought exercise. How long would it take you to use the 4E Power Toolkit to simulate the 3.X classes & prestige classes in the Complete (Splat) books? And could you release them under GSL before Wizards do? Enquiring minds etc.
Other systems have a different pool to draw on:
Eposic.org has a number of random generators (including a nice batch of Tunnels & Trolls stuff) as well as more generic (FUDGE dice) and system-less tools.
Role-Playing Assistant (RPA) - A veritable Swiss Army application - it's been around a while and I was reminded of it's utility the other day. We're doing well if we forget applications this good...
A character generator for the following systems: AD&D 2nd ed, D&D 3.0 and 3.5, Star Wars (d6 and d20), d20 Modern, Cyberpunk 2020, Alternity, Rolemaster (2nd ed), In Nomine (French) and Dragonball Z (this is beta mode).
It also includes a name generator, spell book generator, monster and encounter generator, weather generator, NPC party generator, dice roller, fractal mapper, DM character summary and D&D3.0 treasure generator. You can also create your own tables and modify outputs as well as generating templates for various uses and export the results by e-mail.
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