Federer came from a genernation where courts and ie playing styles were still very much polarised. 2hbh wasnt the defacto technique and SnV was still a dominant playing style. Feds game was more tailored toward grass/hc in his early years and only post 05 did he really tailor his clay game heavily to be more consistent at the expense of his grass/hc game (imo).
Yes he could have done more but it took awhile for Fed to "get it" (his was a mental menance also in his young years) and go to the next level, similar to Djokovic back in 2011.
I think timing plays a big role and Djokovic has had the perfect timing to then end as the current slam winner. He was always the chaser and never had to deal with young guns til very late into his career. I tend to think Fed had it the hardest via pioneering the path forward on how to do well beyond 30s (never done before in open era), adjusting his game to slowing conditions on all courts and having to deal with not just 1 younger ATG but 2.
As a matter of fact, you put Fed in Djokovics shoe very high chance he ends up the slam winner by cleaning up the latter part of their career. Nadal is abit of an odd one because his longetivity isnt quite like the other two but if he was in Fed shoes (star 5years earlier) he'd be collectin WB/RG trophies early on his career like Borg so maybe that compensates for it.
It is true that all players are a product of their own time, but we shouldn't forget Federer grew up on clay courts....but his issue was the same as Becker's and Edberg who also played a lot on clay growing up, they simply didn't take well to it. Now that is not a bad thing, but it can also come back to bite you. It is well known Federer lost his first 11 professional matches on clay, so he truly had turned himself into a more fast court player.
Federer's first big title was on clay, lets not forget that, he won Hamburg 2002 and he also made the final of Rome 2003. He could play, but he simply couldn't get his game to work at the elite level on it, heck even in 2005 he was playing his hard court style of tennis there, 2006 was where you actually saw a more clay style version of Federer, but it came too late, his window to achieve success early on was shut down, and now he had to deal with a peaking Nadal.
I do agree that Federer did some pioneering, but I don't think this was all Federer, I think he took a lot of it from watching Agassi. Lets not forget, Agassi was winning slams into his 30s, and even played Federer himself in the USO 2005 final when he was 35 and 11 years older than Federer. Agassi was showing Federer the way first....Nadal then followed Federer, and Djokovic followed Nadal.
Maybe Federer wins the slam race if he starts the last of the three, but maybe he doesn't. Federer was a hot head and quite volatile in his early days, and quite honestly that young Federer would struggle immensely if he was dealing with 2010 and 2011 versions of Djokodal if he was teenager....I mean, Agassi schooled him at USO 2001 when he was 20.
We will never know the real truth, everything happened the way it happened in the end.