@Xnero There is a point to creating GitHub Issues. Creating an issue makes a record of it, which allows anyone to work on the issue when they have time to work on problems. If something is not in an Issue, then people don't necessarily know about it or remember it when they are looking for a task to do with some time they have available. It also allows things to be organized and prioritized, both by the project and by each individual.
A ping in chat is reasonable if you're just thinking of something, or just encounter a problem that might be addressed quickly, or, particularly, for problems which need to be addressed immediately.
However, on the receiving end, a ping can easily feel like a "please work on this now" request to the person who is being pinged (at least to some extent). This is particularly true if pinged repeatedly. The person pinged may, or may not, be able to work on it at that time (for whatever reason). This can be quite frustrating for everyone involved: you feel the problem you've identified isn't being addressed; they feel put-upon, etc.
It can also end up being less efficient development, if done to excess. Each ping can end up being a context switch, which, just by itself, even if nothing is done other than reading, consumes time and reduces mental focus on whatever the person was working on. To a large extent, people on the receiving end learn to deal with such things by just ignoring pings/such interruptions during times when they are busy, but that can lead to the person sending the message feeling ignored.
I'm not saying "never ping", or anything close to that. I am saying that if you want something done in a project like this and a quick ping doesn't lead to immediate resolution, the next step should be something like opening an Issue on GitHub. I know that feels like more work, and I, too, am guilty of not doing it as often as I should, but it is a good/important way to proceed for many/most problems, particularly development related ones.
For this issue, it would be good to have a GitHub Issue about changing Rails to using HTTPS for generating links, such as this one. There are quite a number of places in the project where "http:" URLs are used; some are needed, but others not. It would be a good low-priority thing to go through them and change to "https:", where appropriate.
However, for the specific case of having "http://" links in the messages which MS sends to SD to post in chat, I did look at it a bit further and there's an existing monkey-patch in SD to convert "https:" links to protocol-relative links. The exiting implementation of that was likely to corrupt some question titles when sent from MS. Thus, I've changed it to both make it much less likely to corrupt a title, but also to convert "http:" links to protocol-relative.
However, having SD change to protocol-relative URLs really isn't the right place to resolve the underlying "http:" address issue. It just masks it from affecting MS messages.