The specific thing that bothers me when looking at the might have beens is that Andy always seemed to run into injury issues when he was at his peak.
In 2012 he was clearly pushing to make the final breakthrough and after a heartbreaking loss at Wimbledon he then stormed to Olympic gold and then the US Open title. Heading into 2013 Federer looked to be on the decline and Nadal was not doing much away from the clay and so it looked like it was set up for Murray and Djokovic to dominate for a while. Sadly, the occasional back problems that had plagued Andy flared up early in the year and he had to skip some tournaments and although he did win Wimbledon he shortly followed that up with back surgery and then took a long time to get back anywhere close to the level of the tennis he had played before injury. Novak then got to feast with basically the other 3 of the big 4 largely sidelined or struggling for fitness over the next 18 months. I genuinely feel Andy would have won a couple more slams in 2014/15 without the back issues as he was playing at the same level as Novak prior to the surgery.
Finally in 2016 Andy was back at his best, the 2014 season had been tough as he had been unable to train properly due to his surgery and then in 2015 Novak was truly in his pomp and Andy needed to dig deeper than ever before to match him. 2016 felt different though and after pushing Novak hard through the first 6 months Andy broke through with his second Wimbledon and second Olympic Gold before adding a clutch of smaller titles as a prelude to winning the Tour Finals. Roger was back playing at a decent level and Nadal was recovering too but there was little doubt that with Novak seemingly having lost a little drive 2017 was set up perfectly for Andy to enjoy his time in the sun as Novak had a couple of years earlier. Of course instead Andy struggled badly with illness at the start of the year contributing to a poor AO showing and then fatefully there came that grueling match against Wawrinka at the French that turned his bothersome hip issue into a chronic problem that has now ended his career.
I know it is impossible to predict what would have happened but I remain convinced that if either of these injuries had been averted, or at least had occurred 12 months later than they did, Andy would have won more titles at Grand Slam events. The injuries were devastating enough but I cannot help thinking that they were especially cruel due to their timing.
Also not his peak but just after reaching the top 10 in 2007 he had that wrist injury that took him pretty much a whole year to get back to where he was before. He wasn't far behind Novak when it happened, but in the meantime ND made his first slam semis and would go on to win his first one, meanwhile Andy was just fighting to get back into the top 10