My main problem with 5E is that is vague in a lot of areas that I had to go back to 3.5 to get my answer.

I just went back to 3.5 and I’m glad I did. It is the best edition.

In the long-term groups I've DM'd for the last 8-9 years (maybe 30-35 players), we've started on 5e as that'd the one that people have heard of and seen on YouTube, Twitch, and the like. It's a decent set of rules to get started on - it makes compromises for ease-of-play but falls short in some areas because of that - but I've then had maybe two-thirds of people want to move to something else after a year or two.
       Half of them wanted something more crunchy with more tactical combat and a greater degree of character customisation. These people have moved to 3.5e or PF1 (and PF2 now but I don't run that at the moment) accepting the greater complexity of the system over 5e.
       The other half, being more interested in role-play rather than rules, have shifted over to 2e (or an even lighter OSR clone) with its more abstract combat system and fewer codified options for characters (we don't use all the "splat books") which they enjoy for more narrative play and they don't mind the "rulings over rules" approach. They're all good systems - it just depends on what you want to play.
       5e can certainly be tweaked in either direction from its middle ground, and we did, bringing in elements of 3.5e, or dropping aspects of 5e, but we eventually figured why not just play the other systems?

Savage Species and Epic levels are only scratching the surface of all the subsystems 3.5 had. Any battlemaster fan in 5e would probably just look at Tome of Battle, and wonder why the battlemaster wasn’t 1/10th as cool as those classes.

<Pathfinder first edition has entered the chat>

Monte Cook took most of the improvements with him from his time with MERP (unified action resolution, Saving Throw Categories, skill ranks).
3E is the biggest step since OD&D and we should eternally thank Monte for this (and the folks at MERP).

Love 3.5e. I still run a PF1e game, but still utilize my 3e/3.5e supplements and adventures on occasion, since conversion takes little work.
Expanded Psionics Handbook and Draconomicon are still my favorite supplements and the Sunless Citadel adventure path series (for lack of a better term) was one of my favorites to run.

I miss prestige class. A lot.
Its the level of customization that 5e needs.

I'm glad Internet Archive has so many of these rulebooks because i get to have and read on what I've missed out on.

I would type something about how goofy 3E is but I gotta check a massive chart to see if it provokes an attack of opportunity or not.

For me personally it was the E6 3.5 variant that really hit the sweet spot. Of mild interest is that it had BAB max out at +6 on the best progression, which also happens to be the limit in bounded accuracy, not a coincidence I suspect :)

I think every edition has their pros and cons. I started with AD&D 2nd edition, and for me this will always be my favorite edition.

Savage Species!! It is my favorite 3E book as a DM. It helped me learn how to balance Dragons and Centaur PCs can playing alongside Halfling PCs.

With the release of 3e, WOTC dropped the "Basic" line of rules and dropped the name "Advanced" from D&D 3e. 5e is just the Basic ruleset that corresponds to 3e.

3.5 is king IF the DM gets vice-like control over the madness.

3.5 also had "feat prerequisites" where, in order to take the feat you wanted, you had to take other (often crappy) feats you didn't want. So, it wasn't all good. I do miss prestige classes though.

I love D&D 3e where a faild CON-save vs the Disintegrate Spell meant instant death.

From a purely comparative perspective, having DM'd OSR and hybrid simple systems, assorted OGL based games, Beyond and 5e, as well as short runs of Burning Wheel, Genesys, and the Dark Eye, 5e is one of the most distinctly convenient systems to teach, run, and play. The primary strength of D&D when compared to many other systems is its intuitive mathematics and simple combat/action resolution. 5e vanilla made a huge effort to leverage that simplicity.

D&D's biggest weakness is it's inconsistency in maintaining it's intuitiveness and simplicity in it's magic system and expansions, awkwardly tacking on rule after rule for each new spell or power creep-balancing melee feat/skill.

This inconsistency driven by the core strength of the simple resolution system and demand for spells and expansions inevitably introducing complications of and system-weakening power creep has always been D&D's systemic problem. The inconsistency in it's "each spell a rule" departure from the base resolution mechanics also explains why creep is most aggressive in casting classes. No one argue for bringing magic in line with the base resolution mechanics of the d20 system, because to most players, power creep and cheating the fair resolution of simple d20 attack rolls is their unconscious goal in the game.  

Don't take this as baking any version of D&D. I've DM'd or played all of them, D&D is awesome. I love it. I loved the expansive resources available in 3.5 and the ease of introducing players to 5e. But every version carries flaws along with it's benefits. None demand a single type of story or gameplay. They are all filled with pros and cons and our favorites are entirely subjective. Over the past few years, debates over which versions are better or worse are largely pressed by people who enjoy different modes of play talking past each other, often belittling each other's tastes and goals in playing ttrpg's, more than discussing any systems' merits. After all, a simplicity focused player who enjoyed AD&D and returned to 5e and plays entirely on paper might not see the expansive options in 3.5 as a benefit, while an OGL Pathfinder die hard with crates of painted minis would be bored senseless without a chance to debate tactics on the board around the table as they look for a visible edge running recon on a Vampire Lord's lair. After a while, debates between people looking for entirely different games just seem pointless and contrived.

Enjoying this miniseries :) 3rd is where "players should have the power" really gained steam. WotC saw that players were the larger market, so they leaned hard into player-serving books & design, vs 2e's setting boxes and campaign guides.

I'd argue Linear Fighters, Quadratic Wizards was at its worst in 3.5e as well. 4e elegantly addressed that, as well as making DMs happier on multiple fronts (goodbye CR!).

Great video, content and quality, Jay! Glad the algorithm let me know you were making these. Completely agree on 3E/3.5 and I've reverted to running it. Absolutely love the system, and whilst 2E will always give me the best nostalgia fuzzies, as a system 3E is just top tier.