If you owe that much wealth to a city, then that means that city has put out that much wealth, one way or another, on your behalf. The Hellfire Club Hellfire Shirt worst they can do is send people to try to motivate you, but, so what? If you default, the city’s economy collapses, if it hasn’t already. It will likely have problems paying its guards or soldiers or courtiers or any other number of things. So, how do you resolve this? Instead of investing your money into paying back the debt, you invest your money into the city’s infrastructure. You buy the constabulary, the services, everything out from under them. You ensure the machinery go on, and then…
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You can call this the “Grand Theft Auto instinct,” as it reflects a lot of Hellfire Club Hellfire Shirt ’ behavior when they first get their hands on GTA and realize they can hit pedestrians with cars practically all day. And, like going around randomly crashing cars in GTA, murderhoboing gets boring after a really short time. That goes especially for the DM. It gets dull watching players do the same things all the time and watching every adventure result in the players taking a baseball bat to everything you prepared. You eventually go, “okay, we get it,” and want either players who invest more in their characterization, or you want to see objectives and interactions that are more sophisticated or structured.
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Huzzah! He tries to grapple the guard and Hellfire Club Hellfire Shirt an attack. You rattle some dice around, not actually caring what they say as the guard “defends” himself. Barb’s hooked his bindings around the guard’s throat and is now using him as a meat flail. Why? Because you don’t want these idiots to die, it’s neat, and everything saner has failed. In the ensuing melee you rattle dice around some more, and press the Players just enough that they feel that they’re challenged, yet still escape mostly intact. Now the key to this improvisation is that you have to work with what the players give you. If they do nothing, well, it’s the gallows then. As long as they keep working the problem, keep giving them things to work with. And damnit, escape by meat-flail is better than anything I’d have come up with myself.
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I was hoping Delores wouldn’t become a Hellfire Club Hellfire Shirt aggressive rooster, as my recently deceased “Lance” had been, before passing on to “rooster heaven” with the assistance of a local coyote. The rooster I currently had, Gordon, was a sweet boy and was very happy to have Lance gone. Lance had been a fierce rooster who attacked literally every moving thing but the hens and me (displaying extreme good taste and discretion) and I was not prepared to live through as second several years of yet another “attack rooster”. Neither were the neighbor dogs. Nor were the neighbors, for that matter. I really didn’t think this would be a problem, as Delores was such a sweet rooster – showing no violence or aggression at all, and just wanted to sit on my shoulder (rather like a parrot) and look around. He’d snuggle against anyone’s neck or in anyone’s lap who would hold him and he adored being petted. Delores ran around digging for bugs in the lawn – but was just as happy sitting by the kitchen sink watching me trim vegetables or whatever. He made (as all my chickens did) a truce with the cats and was friends with the goats, horses and my other rooster, Gordon. They all slept together in the barn at night.