It's not fair to compare the two without mentioning all of Romo's injuries which kept us from making the playoffs at least once or twice more either in 2008, 2010 or 2013.
It's also not fair when you consider that the Cowboys circa 2016, 2018, 2022 are much better run than they were circa 2006, 2008, 2011, etc., with consistently better rosters outside of one-off's like 2009 or 2014.
With that said, I think Dak is arguably at the same point that Romo was at in 2014 where his experience/knowledge of the game evolved to an elite level while his body was still able to perform. Of course that all went to shit in 2015, and he was a few years older at that point than Dak is now, but luckily I think Dak is at least close to where Romo was in 2014 in terms of everything coming together.