I joined a node project that was stuck on 0.12 while 7.0 was being developed. It was a shit show to get us to 6. As I recall, 10 was a little tricky, 12 and 16 had a lot of head scratchers. I finished the 16 upgrade more than a year after the last person tried, and it was a dumb luck epiphany that kept it that short.
I had a similar experience with emberJS when it was still young. Every time I picked the project up I had one to two hours of upgrade work to get it to run again, and I just had a couple hours to work on it. So half my time went to maintenance and it wasn’t sustainable.
I’m trying a related idea now in elixir and José may be a saint. Though I fear a Java 5 moment in their future, where the levee breaks and a flood of changes come at once.