3. Tax benefits. I have been told by clients that they have petitioned the county to lower their taxes based on the reduced "value" of their home without a pool. I have not verified the validity of this so check for yourself.
4. Having another set of eyes "AKA Building Inspector" visit your jobsite verifies that the pool removal process is done to the satisfaction of local requirements and keeps your contractor on track as well.
5. The cost of going back and permitting and unpermitted pool will far exceed the oringinal cost.
The only advantage to not obtaining a permit is to save $100-$500 in permit cost . In terms of Risk / Reward I feel there is no question here. Hence my "Why not" statement.
If your contractor tries to talk you out of getting a permit or tells you to take care of the permit I would suggest finding another contractor. An experienced pool removal contractor can handle everything for you in far less time than if you do it yourself.
Dig & Demo