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Notes -
Kind of, but it's not as big a hurdle as you imagine it to be, though you do have to at least loosely keep up with new (= more filtered) snapshot releases and general happenings. It also depends on the exact things you do, you probably don't need the big-dick 2k token stuff for general conversation, ever since I burned out on hardcore degeneracy I haven't really been updating my prompts and they still mostly work on the latest GPT snapshots when I'm not doing NSFW shit.
As for jailbreaks, this list is a good place to start. Most jailbreaks come in the form of "presets" that rigidly structure the prompt, basically surrounding the chat history with lots of instructions. The preset's .json can be imported into frontends like SillyTavern with relatively little hassle, the UI can be intimidating at first but wrangling prompts is not actually difficult, every block of the constructed prompt has its own content and its own spot in the overall massive prompt you send to the LLM. Example. The frontend structures the prompt (usually into an RP format) for you, and during chat you only need to write your actual queries/responses as the user, with the frontend+preset taking care of the rest and whipping the LLM to generate a response according to the instructions.
Unless you're just talking to the "bare" LLM itself, this approach usually needs a character card (basically a description of who you're talking to), I mentioned those in passing elsewhere.
To contextualize all this, I unfortunately have no better advice than to lurk /g/ chatbot threads, it's smooth sailing once you get going but there's not really a single accessible resource/tutorial to get all this set up (maybe it's for the better, security in obscurity etc).
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