on Music:

DD insisted she start violin at 2.5 (saw my old tiny suzuki violin). The lessons were very inexpensive so I agreed (they are very expensive where we moved so I wouldn't have started her here at that age). She likes it, but doesn't love it. She could play as well as the 4yo's at her recital before she turned 3.. but to what end? She's sort of indifferent about it and doesn't care to practice. She is now just-turned 4 and still playing suzuki. She likes the concerts so doesn't want to quit but doesn't like to practice. She is the type that wants to try everything but doesn't want to continue so we are letting her keep going even though she just wants to play so she can play in the concerts. Just FWIW.
Your DS sounds more musically inclined.

Preschool: I would totally do it if the school allows. It sounds like your DS barely misses the cut off so not that big of a deal anyway. DD does Montessori and has been in 2 different schools. The first was a younger class (still 3-6) but they didn't challenge her. She went to school crying and hated it despite the teacher. We moved to a new school & went in with showing her reading skills, math, ect. She loves it. LOVES it. They have her read to them at her level, does the math of the older kids. She has fine motor issues & they are addressing that too. Not every montessori is the same - even though I loved her first one, it just wasn't a good fit for DD.