How many times did endosymbiosis occur?
Well, it seems quite obvious that it was not a single I-eat-you-but-you-survived act but rather a convergence of endosymbiotic and host species into a greater and greater cooperation. 
Of course this leaves a question if there was one or more species of endosymbionts involved.

Mitochondria are a very primeval story forced by the oxygen catastrophe, so it is hard to say, although great majority of mitochondria seems to have a single origin.

Plastids are much more divergent, however it seems that they did originated from a single source, diverged into chloroplasts, cyanelles and rhodoplasts and were later mixed up by numerous acts of secondary and even tertiary endosymbiosis (plus a further evolution); this variety can be especially seen within Euglenas, and they are the main group investigated in this manner.