As a former VHLM GM's in the 80s, I get your valid complaint. Pitching to waivers was at the time really a grind, as you wanted to be the first one to pitch, for reasons already mentioned by others. I would like to add a little twist to it as well. If not the first pitch was taken, a good graphic often helped. Luckily, back then, @Ricer13 was so kind to make one for my waiver pitches, and I am sure it got me the odd player I would not have gotten otherwise.
Now it is more of a level playing field and GM's cannot exaggerate the roster situation to newcomers as much as back then (and I do not mean that it was done maliciously, some teams had no picks and almost no players in the roster, they had to sugarcoat their situation without outright lying in order to attract players). Also now you are given a 'pitch' for all the teams in the league and can make a decently informed decision what team you want to join. Back then maybe five teams were pitching, because competing teams with a roster of recreates would not like to 'water down' the TPE average by signing a first gen who would 'steal' time from the maxed players.
If I remember correctly, a rule was then implemented/in place that all teams had to pitch if they did not have a 'full roster' (I believe it was two lines and a netminder, but do not quote me on that). As you can imagine, such a rule is a b**ch to enforce and put unnecessary strain on GM's and Commishes alike (I for example come from the Central European time zone and it was not always possible to be on top of all the NA new-arrivals).
So, yeah I feel the nostalgia and do not disagree with you. I still think the current solution is more balanced and sustainable than what we had before.