My main practice for the better part of the last 24 years has been vipassana meditation. So, my recommendation would be to undertake a residential retreat of vipassana meditation in a tradition that you feel comfortable with. I recommend that over a selection of Dhamma books because I think what you seem to be after is the development of experiential wisdom (bhavana-maya-panna) rather than developing a purely intellectual understanding of emptiness in the Theravada context.
But if you are looking for a very good Dhamma book on vipassana in the context of the panorama of Buddhist meditaton then Nyaniponika Thera's iconic work The Heart of Buddhist Meditation is unbeatable.
My own teacher is SN Goenka, and if you are looking at retreats, you could also look at retreats organised by International Meditation Centre (IMC), and the students of Ajahn Chah and Mahasi Sayadaw. And I am sure other practitioners here wil advise you with regards to the styles of vipassana retreats that they have attended.
“No lists of things to be done. The day providential to itself. The hour. There is no later. This is later. All things of grace and beauty such that one holds them to one's heart have a common provenance in pain. Their birth in grief and ashes.”
- Cormac McCarthy, The Road
Learn this from the waters:
in mountain clefts and chasms,
loud gush the streamlets,
but great rivers flow silently.
- Sutta Nipata 3.725Compassionate Hands Foundation
(Buddhist aid in Myanmar) • Buddhist Global Relief