Usually doing a high one like CME/IFR covers all things below.. This "Slow and Draggy" thing is over emphasised. IMHO. Once you understand the Issues an demonstrate competence you are unlikely to forget or ignore them.. Plenty of Instructors would fly 5 different planes in a day.
At the Other end of scale, Complex Heavies, Multiple Endorsements are Not allowed for fear OF CONFUSION. You will be Licenced to fly ONE RPT type on which you are current. Flying Light aircraft excluded as Long as Flight time limitations aren't exceeded. Jumping into things like A Pitts are even encouraged by some Progressive Airlines. Nev