Isn't there a contradiction in Baba telling Damu Anna his 'plates will always be full' but then also advising him to abandon worldly desires? Was he supposed to pursue wealth or not?

This question contains a couple of misunderstandings that are clarified in Chapter 3. Firstly, the recipient of this advice was Annasaheb Dabholkar, not Damu Anna. Secondly, there is no contradiction in Baba's guidance. The assurance that "His plates are always full" was not a promise of vast wealth from trade, but a guarantee that his essential material needs would be met if he dedicated himself to Baba's service. The subsequent advice to abandon desire is the next step on the spiritual path. Once a devotee is free from the anxiety of basic survival, they can focus on the higher goal of self-realization. By understanding Baba's true nature as the all-pervading Self, as explained in the text, worldly desires naturally dissolve, leading to ultimate peace and contentment.