Like @MarkUCLA I purchased my lifetime subscription in 2017 in my case in June so just over 6 years with Roon and no regrets.
'Fraid I also fit the age group of many users; just coming up 70…
There have been highs and lows but overall Roon keeps moving forward and, as many have said, for the price of a piece of HiFi kit it gives so much more. My system stands me in circa £16k and Roon is probably the best (and almost cheapest) single component. No other part of my system introduces me to new music (and re-introduces me to old) in quite the same way.
I know that there has been substantial criticism of Roon from time to time. Sometimes with justification. But since ARC, things feel much more positive in the community. I may be wrong it’s just my perception but it could at one time be a negative place to hang out.
I love the tinkering aspect as well. I have tried all sorts of cores from Mac, Windows and VM Rock (which was very stable but just rather inconvenient and inefficient). I have now happily settled with Rock running on an aged 2013 i5 MacBook Air (therefore Intel based so applied a scratch build from the standard Rock install - no Apple software in sight). This is super stable. I have three Raspberry Pis, two running extensions with Audio Entry Points and end points and the third running Ropieee XL this latter I plan to use as a Roon end point extending it with preset buttons using the API to root My Radio stations to the end point. In short it gives me lots of opportunities to do totally unnecessary things just because I can.
So to get back on topic I don’t currently see me moving away from Roon as long as they survive and prosper and at least one integrated quality streaming service holds up.