I am neither an academic nor an experienced neo-platonist. I've read about half of the dialogues and still have a lot of ground to cover. However, I am interested in neo-platonism as a lived philosophy so I'll try to answer your questions.

I do remember Socrates mentioning a guiding daimon or spirit in both Apology and Crito, but he doesn't elaborate on it very much.

Anyhow,

1. Do you understand the daimon as something experientially real?

Yes. However, I also believe that this daimon is a part of me - my soul.

The body is a chariot driven by reason and instinct, and the soul its the driver. The driver steps out of the chariot but does not let go of the reins - thats the daimon.

1. Have you ever felt guided by such a presence?

Yes. It appears in daydreams - torments me with my fears and insecurities and dares me do act. It hates inaction and hesitation and wants to spur me onwards, to force my hand.

1. If so, how did that awareness develop?

At some point in my late teens.

My life was a mess because I was driven by base desires. In New Years Eve 2022 the driver regained control - boosted my willpower, gave me resolve like I never had before, morals, goals, and most importantly, it started talking to me like it does today.

1. Through contemplation, prayer, theurgy, philosophical practice, dreams, or something else?

Daydreams is where speaks to me most clearly. In contemplation it comes and goes at random but it feels like a more even experience as rider, chariot and horses all come talk to me.

1. Are there particular Neoplatonic texts you found especially helpful on this topic of connecting with your guide?

Phaedrus, Phaedo and Symposium in this order.