Ok try this- model it the same way you would model a share buyback.
1. Compute the ratios before - no Bob 2. RS per terms in filing (equity flows away from common to insiders in this step) 3. Cash appears on balance sheet for free (Bob cuts check) 4. Preferred transfer to bob (equity flows away from insiders only in this step) 5. Do 4 until Ratios match to step 1