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Wondering if anybody else has pushed forward with an less than ideal technology stack and regretted it? Success stories also welcome..
If it is just that it is no longer fashionable, that is not a good reason.
For everyone who has trouble using older tools, there is somebody who tries something new and goes through hell because of that.
Learning to do the basics in a different way can be exciting and fun for a while. You read blog posts and tutorials that have beautiful layouts and are made by people who write snazzy things on Twitter. Clearly this is a project where cool people hang out.
Then you have to get to work, and suddenly you're having to google everything you previously knew how to do. So maybe someone from the cool gang can help you? You get into a rather fascinating discussion about framework internals, and even start considering that you could perhaps contribute something to this project...
Meanwhile in the real world, you had an actual project to do, but tinkering with the new stack has taken all your time so far. I've seen this play out too many times. Wanting to learn the new thing is 99% about trying to avoid the real work which will inevitably be boring at some point.
What is it that you think is wrong with your current stack? If it is just that it is no longer fashionable, that is not a good reason. For everyone who has trouble using older tools, there is somebody who tries something new and goes through hell because of that.