I'll admit to not following the whole thread but surely the best answer to the "old programs not running on new OS" problem is to adopt the two computer strategy. One computer isolated from the internet running the old programs that are more than good enough for the jobs we need them to do and one on the internet running the latest OS the get the bug fixes, security stuff and compatibility with the current versions of websites we use.
These days basic computers powerful enough to run the internet stuff are relatively cheap and good quality older computers to run our working programs will last for many years. Most of us are quite happy using machine tools of some vintage, I'm 61 and one of my machines is older than I am, so seems logical to take the same view when it comes to working computers. Only time you need a super duper computer on t'net is if you a re into interactive games and heavy duty film streaming.
Reflecting on my last upgrade cycle about 3 years back I'd have saved a fortune going two machine. OK it was Apple kit but principle is the same. Went from G4 Power PC desktop and 17" laptop to Intel MacPro 5.1 and 17" laptop to Mavericks OS via Snow Leopard. Over £2,500 for the computers and monitor over £1,500 for software updates to gain pretty much nothing in terms of what I actually do. 20-20 hindsight says less than £1,000 would have got a Mac Mini and new monitor and been just as effective. Now the iPads have got more oomph stuff and flogging off the new gear.
The one machine does all idea seems to have run its course.
Clive.