I would first practice cutting in and getting a smooth line. And you'd
need a good brush -- I haven't been impressed by the brushes I've seen
at HD or Lowe's. My favorite is the Porter paint line. If you don't
have a Porter in your area, check out some brushes at MAB or
Sherwin-Williams.

You're way is more time consuming and, by the way, painted baseboards
[and casings] are typically caulked to the wall. Honestly, I've never
seen it not caulked.

If you're intent on masking, why don't you mask the ceiling instead of
the wall? Textured ceilings? I think you'll need the wait more than a
day -- just because the paint is dry doesn't mean it's cured. Also,
You'll need blue tape [or one of those other colors that won't pull off
fresh paint]. AND, whatever you use, make sure you get flat tape.
Regular masking tape has a texture to it, and will allow seepage unless
you use something flat and hard -- like a putty kife -- to flatten it
against the surface. Or use flat tape.

Conventional wisdom is conventional for a reason, although I do things
in this order---
1. Ceiling [so you don't rain down on everything else you've done]
2. Casings [window and door trim] [cutting in the walls against the
casings is easier than vice versa.
3. Walls
4. Baseboard