theRPGsite - Holy crap, an honest to God forum. This is the Stoa where I go to watch bad ideas die. If you're at all thin-skinned, avoid.
Medieval Fantasy City Generator - watabou has an awesome one-click tool to toss a city down. I recommend using it with some flavor of random city system like - Vornheim or grab the city crawling rules from Last Grasp; alternately use his Cörpathium system.
I mean, if you're a real psycho, you could expand the map and detail it.
While you're there, Last Grasp has generators for nearly everything. If you can't find one, make it. You can save the links in your bookmarks for the seat-of-your-pants DMing I prefer.
The Angry GM is good for getting my focus back, and solving problems I didn't know I had. And creating new ones. He's a dick.
The Monsters Know What They're Doing - and so does Keith Ammann. I bought the e-book, by way of thanks but the blog is excellent. While it is very 5e system specific, no matter what rules you use, his habit of deconstructing what a monster is, and how that should drive its behavior, should be studied.
I switched from Evernote to OneNote for the purely pragmatic reason of having been paying for it as part of Office, but then I discovered Cryrid's templates and it has been nothing but WIN. Hands down this has worked out best for my scatterbrained DMing.
Goblin Punch has me half-convinced I've been doing it wrong for a lot of years. Funny, insightful and awe-inspiring by turns, if you look at NOTHING else here, you must read why God Hates Orcs. In fact, f*ck this blog and go read his.
Scribd is my go-to library these days. Tons of books and audiobooks to mine for inspiration - poke through the Appendix N reading list and go wild.
I prefer to map on paper, but Dungeon-scrawl is great for old-school pretty maps and gets bonus points for the name too.
Online Gaming Specific
Now, I'm strictly a miniatures and terrain guy. I'll -tolerate- theater of the mind, but online is strictly for emergencies. Since we're still limited by the Kung-Flu, I've had to go remote.
Token Stamp 2 is a good way to get stand ins for your miniatures.
Owlbear Rodeo is the essentials, without getting roped into a subscription, or having to go back to school to figure it out.
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