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I think it depends a lot on the country you're in, especially the laws, and the size of your city and who you're buying from and what they sell but personally, in the days when I used to do this stuff, it would always be through a friend, and associate, or a friend of one of those. Some of the people were selling to make ends meet but even they were still small-time and so they were definitely more amateurish than someone who is effectively operating a business and it showed in how they managed their affairs.
If you are busted, it isn't going to save you.
But if they're doing dragnet surveillance of the communication that the dealer is engaged in, they might not be assigning a whole lot of resources to the task - it might just be a matter of getting names and identifying the candidates who are the obvious ones but the other minutiae gets overlooked because it isn't considered worth the cops' time investigating every single contact. (This is where the benefit of small-time dealers comes in - they are almost always going to be sloppier with everything they do but if they aren't moving tons of product then the cops are less likely to treat it like they're busting a ring and more likely they're going to take down a couple of people who are the easiest targets before moving on the supplier. In this situation it's a bit like that adage - you don't have to be the fastest runner to get away from a bear, you just have to be faster than the guy next to you.)
Or if it's something where they need to get a judge's signature before they can target you for surveillance or searches then they likely need to at least have a semblance of cause before they will get the go-ahead and simply messaging to ask if someone is free to catch up isn't likely to meet that standard. If it does happen to get the sign off, there's a chance that you'd be able to contest shit in a courtroom if you did get busted but that all depends on your local laws, how corrupt the judiciary is, how much the police think they can get away with when they lie in their testimony and all of that. But cases do get thrown out due to failure to adhere to the correct process often enough that it can be worth taking a shot at it.
Look, I'm no sovereign citizen and I'm not under the impression that you can just utter the correct magical phrase which was taught to you by a more senior ~~constitutional wizard~~ SovCit and that will dispell any charges against you but at the same time maintaining plausible deniability and covering your tracks is always the best practice. Even if it doesn't prevent you from getting charged, depriving the prosecution of evidence and especially the stuff that clearly implicates you will make their job harder and it can lead to reduced charges, lighter sentencing, and better chances at a suspended sentence or getting parole earlier and stuff like that.
If there was one simple trick to this either everyone would know about it or they'd ban it. But most of the time people come unstuck because of the cumulative effect of a series of bad choices and if you can minimise the bad choices then you mitigate the consequences.
(It just occurred to me since I was typing out this comment and thinking about this Discord server - does discord automatically strip metadata from images? Because if not, goddamn that's another massive risk to go exposung yourself to.)