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Been years since I've posted or really read on /p/ so here's where I'm at now as a newly profitable portrait photographer with my wife:
Canon 5D mark III, two bodies, two canon grips
Canon 28-70 2.8 L (no, not the 24-70)
Canon 70-200 2.8 IS USM
Canon 35 f/2 IS USM
Canon 40 2.8 STM (had it since it came out)
Canon 50 1.8 STM
Canon 85 1.8 USM
Canon 100 2.8 Macro USM
Canon 20-35 USM
580EX
430EX
Yongnuo 568 EX II x2
Yongnuo 685
Yongnuo 622c x4 Tranceivers
and honestly I shoot most of my off camera flash with 30 inch shoot through umbrella's or 45 inch brolly boxes because I can't be fucked with lugging around gridded octaboxes.
Basically, I set out to get adequate gear to shoot weddings as cheaply as possible. The 28-70 2.8 is half the price of the 24-70 2.8 . The 70-200 IS gets you 90% of the IS II and is sharp enough. The 100 Macro is only really for ring shots and close ups as the lens is redundant with the 70-200 2.8. The 50 is the best bang for the buck in Canon's lineup. The 40 because why not. The 35 f/2 IS is easy mode in low light. The 5D mk III body is the best bang for the buck and I got two in the 40-50k shutter count range for about 1k a piece.
pic related is still my favorite piece of kit.