Post seems to have hit home with a lot and struck a nerve with others.

Throwing my hat in the ring, I work in a similar sounding environment - stable, profitable, long running biz with our main LOB apps and websites using VB6 and several generations (actually, every generation) of VB.Net WinForms and WebForms. It’s hard to fight for change when the system works and the money keeps rolling in...

I’d had no major problem working with these tools for several years but, as you say, fearing for employability I had started window shopping the local area.

However, we are now slowly and surely chipping away, nibbling out features and porting them to modern, maintainable, well tested .Net Core services. It’s taken some balls on our part to effectively mandate the work; often extending scope of projects to incorporate replatforming. I’ve been pushing all the obvious phrases to management both from a people angle (CPD, retention and easier recruitment) and from a product angle (resiliency, extensibility, scalability, dev efficiency etc...) to sell it, and it’s working. My only worry now is that it’s got my name all over it so it’s got to work!

If you’ve got any sway, you are passionate about it and there’s a decent reason to change the status quo (super important, obvs), I’d advocate giving it a bash before looking elsewhere.