D&D 5E Considering "taking the 5th" (Edition); questions for those more experienced.

[FormerlyHemlock]

If I had ever played a game with a tactically complex initiative system that was simple and fast I'd probably like it too. But as it is, speed of play and simplicity keep moving higher and higher up my scale of desirable RPG traits.

Good, you should give AD&D-style initiative another try then. It is simple and it is fast. The key thing is not to get hung up on rolling initiative for the sake of rolling initiative. Declare actions, resolve actions. Roll initiative only when action resolutions turn out to be mutually exclusive (average IME: once or twice per combat).

 

[Iosue]

Let me recommend B/X-BECMI initiative, as simple, dynamic, and tactical.

1. Roll initiative for each side
2. Winning side goes first
2a. Movement
2b. Missiles
2c. Magic
2d. Melee
3. Losing side goes next
3a. See 2a.
4. Go back to 1.

Don't worry about declaring actions. Let each person decide if they want to make use of a particular phase.