I get excited talking about this topic because the word 'tawaif' carries so much cultural weight in Urdu poetry and literature. If you're hunting for meaning, a great place to begin is with digitized poetry archives and dedicated Urdu portals where poets' ghazals and nazms are published alongside glosses. Search for the Urdu script 'طوائف' as well as the phonetic 'tawaif' — many older couplets use the Persianized form and reading it in script helps you catch the original connotations.
I also lean on classic lexicons and annotated editions like 'Diwan-e-Ghalib' with footnotes or the 'Oxford Urdu-English Dictionary' for literal meanings. Academic papers and book chapters that discuss the social history of courtesans put poetic usage in context; look for literary studies about colonial and 19th-century South Asia. When a tawaif appears in a ghazal it's rarely just a label — she often represents craft, musical training, sensuality, social marginality, and a space of artistic patronage. Reading the poem alongside a brief cultural sketch changes everything. Personally, pairing a glossary entry with a short essay or an annotated poem always makes the meaning click for me.