I most highly recommend reading or listening to the following lecture, which covers some of the most profound suttas, and addresses issues such as philosophy of language and how it impacts communication, as well as Dependent Origination and relativity, all with regards to the conceptualisation of ‘Self - I am’, as well as the effects of proliferation and imaginings as a direct hindrance to realisation.
It is a brilliant and comprehensive exposition on these issues, by Ven K Nanananda as part of a series of lectures on Nibbana, and presented by Bhikkhu Analayo.