A person who never made a mistake never tried anything new.
To those people who claim that Holydramon isn’t canon evolution of Tailmon. Let’s look at the new re-release Digivice evolutions.
Umm what’s that, no Ofanimon?
Digimon Adventure’s, Hikari’s Tailmon’s Ultimate evolution is Holydramon. It has been showed in Digimon Adventure 02: Digimon Hurricane Touchdown!! Supreme Evolution!! The Golden Digimentals movie. As well as in the Wonderswan games. The only thing were it was showed that Hikari’s Tailmon could evolve into Ofanimon was in the PSP Digimon Adventure game.
The thing is that Tailmon’s Ultimate is dragon like, because Hikari is Taichi’s little sister. Because Hikari can take care of herself, she can fight. Not because Hikari ”should” be with Takeru, and their Digimons ”should” be holy angels.
In the Digimon universe, monsters have a bunch of evolution possibilities and all of them are canon all at the same time.
These digital monsters evolve into different forms depending on context, power, good/evil intent, and many other variants. This is why Taichi’s Greymon can evolve to Skull Greymon, Metal Greymon (Vaccine), and Metal Greymon (virus) - three different forms - and they’re all his Perfect level.
In Tailmon’s case, my headcanon is Tailmon evolves to Ophanimon when she wears the Holy Ring on her tail and to Holydramon when she doesn’t. This is yet to be confirmed, but so far it’s what I get from the official material I’ve come across. I think this has nothing to do with Hikari’s competence itself… This show sure has plenty of moments where the psychological state of the human partner is important for a digimon’s evolution, but that’s just one variant in the middle of many others.
Just throwing my 2 cents. I might be wrong, of course. ^^