Wake up, you over there! :)
I chose Paciencia for the opener: the theme is universally known and loved, and its implementation, although not canonical, is catchy more than enough.
14 de diciembre lightens up the mood; it is playful and comfortable while keeping the energy going.
The third place is where I built the lyrical peak of the tanda: Una carta. It has lyricism, drama, and a strong ending.
I end with El vino triste. While it mixes upbeat passages with darker ones, in my mind it provides a more balanced resolution. In most cases, I want my tandas to be multi-colored and not overly dramatizing or, God forbid, desperate.
I use late D'Arienzo sparingly and with passion. It has so much energy I want to be cautious about when to use it. This tanda comes with Horacio Palma, an expressive singer with dominating but not overbearing presence.
In a typical milonga, I would play this in the latter hours at a point when the dancers needed good beats after a prolonged lyrical session and if I felt like they could handle it.
Yes, the danger is that they wouldn't, and that they would destroy the ronda as a result. Mature audience is required :)