Yeah, you could tell Gabe was getting burnt out around 07-08 as things just weren't working as well as they once did with roster transitions and new ideas getting over. I just wish the company had let him finish out 2008 or at least carry out the last of his plans from October to December of that year. It's like they went in the complete opposite direction of what Gabe had spent most of the year getting the company at with Tyler Black becoming World Champion sooner and whatnot.
From there it was just a domino effect of potential company flagbearers (like Black, Davey, Elgin) getting their due too late, people as champion who had no business being champion (like Aries, Lynn, WGTT & Edwards) and the company either waiting too long to fully get behind someone before they left (see Chris Hero, Claudio Castagnoli, Kenny Omega, Kenny King of ANX) or not getting behind them as much as they should have (see El Generico, The Young Bucks during their second run).
In my opinion, his departure started a 5 year free fall for ROH that mercifully came to an end in 2014 with a properly handled new pool of top stars (Steen, Cole, Lethal, Elgin, reDRagon, etc.) and the NJPW partnership leading to a resurgence for the country. Unfortunately, it looks like we're heading back to dark times again. Now, we have almost a year of weird programs and several potential future World Champions (O'Reilly, ACH, Dijak, Bennett, Cedric, etc.) handled improperly and gone elsewhere plus horribly playing bitch to NJPW whenever they come around to home turf.