His generation is sticking around and remaining relevant, at least in small tournaments, like none for decades. If we use the five-year generations, so far this year Roger's generation (1979-83) has won eight tournaments--one ATP 500 and seven ATP 250s (and possibly another 500 today if Ivo wins). Let's see how previous fared at the same point:
Generation Kuerten (1974-78) in 2011: 1 title, Stepanek winning an ATP 500. This generation would win three more titles in 2012-13, all ATP 250.
Generation Sampras (1969-73) in 2006: 0 titles. Santoro would win two more ATP 250s in 2007-08.
Generation Beckberg (1964-68) in 2001: 1 title. Clavet won a single ATP 250, the last of this generation.
Generation McEnlendl (1959-63) in 1996: I only have info on ATP 500s and above, but the last such title this generation won was Canada Masters in 1993 (Mikael Pernfors).
Generation Borg (1954-58) in 1991: Hard to imagine Borg's generation active in the 90s. I only have info on Masters and above, and the last such title this generation won was all the way back in 1982! That would be equivalent to 2007 for Roger's generation.
Generation Connors (1949-53) in 1986: Jimmy's last big title, a Masters, was in 1984.
Generation Newstase (1944-48) in 1981: Don't know, but this gen hadn't won a big title since 1975.
Generation Ashe (1939-43) in 1976: Actually, Mark Cox won a Masters equivalent.
Generation Lavewall (1934-38) in 1971: Still going strong, with the last big titles being Laver winning two Masters equivalents in 1974. Rosewall won the AO in 1971 and 72, and Gimeno the FO in 1972.
Anyhow, as you can see, I don't have all titles before the 21st century so it become spotty. But it is clear that Roger's generation is showing greater longevity than any generation since, well, Laver and Rosewall (1934-38). Starting in the 70s, with generations born in the late 40s, players started peaking earlier and earlier. Aside from outliers, Federer's generation--with players like Ivo, Lopez, Mayer, Verdasco, Monaco, Kohschreiber, Mahut, Garcia-Lopez, Estrella Burgos, Ferrer, and Roger himself all winning titles within the last two years--is setting standards that I'm guessing will at least continue with Generation Nadalkovic. Rafa and Novak's generation will be the same age in 2021 and, I think, will still be around.
What is interesting to note is that aside from Federer and Ferrer, all the very best of their generation are long gone--Hewitt, Roddick, Davydenko, Nalbandian, Safin, Ferrero, Coria, etc. It is lesser players who are sticking around.