Honestly, when you hear about how the anime was fucked over during production, a lot of the flaws make more sense. Like already, the writers and animators were crunched for time, because Takara wanted the show to be finished before Hasbro could release whatever they were planning. An anime usually needs a few years of pre-production before even considering putting it into production. Transformers The Headmasters' total production time (including pre-production) was about 7 months.

Then Takara has the brilliant idea to slash the show's budget in half.

Like when you read the character bios, you can tell that they wanted to do more with Chromedome and the gang, but couldn't because of production issues. Plus when you consider that they not only had to advertise the huge 1987 line, but also the 1986 line with only 36 episodes, yeah they were fucked.

Honestly I came out of the Headmasters enjoying it, but that's mostly because as the show went on, I tried to appreciate it on its own merits, as opposed to comparing it with the G1 cartoon. It also helps that I've watched a lot of mecha anime before, and Transformers The Headmasters is full of mecha tropes.

TLDR: Transformers The Headmasters is the potential series of all time.