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  1. _MountainFit on

    Unlikely to shift with a derailleur as they have a tooth capacity which they can jump. Usually around 14 max. However, if you add a MTB RD you should be able to manually shift it into the upper or lower chain ring (lower might be able to do with your foot while riding).

    Basically find an MTB derailleur that can take up the slack and give it a go without a front.

  2. 20 tooth jump is possible on a wide range 2x setup but that outer chainring is best switch to the inside of the spider. I’ve shifted an old set of sugino px cranks from 26-50 with a simplex 2x front d and without much issue. With a friction shifter and the right front derailleur this should be fine

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