I demolished a 30 year old gunite pool about this size (15'X25' no jacuzzi) a few years ago. I first pumped out about 3' of water from the bottom of the pool. I then knocked two 12" holes in the bottom of the deep end. I drilled 3' into the soil below the pool and back filled those with 1" gravel. I then broke up the apron and the top 3' of the pool wall into 6" and smaller pieces and laid that in the bottom of the pool up to 3' below the final grade. I still had to haul off and dispose of about 2 loads concrete. The pool wall was about 6-9" thick with rebar 12" oc. I used my LX565 skid with a breaker to do most of the work. I had loads of buckshot hauled in and we jetted that into the concrete layer. Then we hauled in clean fill dirt and compacted that with a vibratory roller up to within 12" of the top of the final grade. The final 12" we back-filled with topsoil (also hauled in) and compacted with the roller. It took about a week to wreck out and back fill the pool including hauling off the old pump and filter, putting the fence back up and general clean-up. Planting was by others. Seems like I charged about $10,000 for the job and the customer was glad to get it done for that. He had received several other bids prior to mine. Be sure to include permits and insurance. I checked back with the customer just the other day to see if he had seen any settling. He had not.
I recently bid $21,000 for a pool demo. It is a somewhat larger pool and has a 6'X18" rock wall enclosing it. There is only a 3' gate for access. My bid includes $5,000 for having a rock mason open a 10' hole in the fence and then building it back when the demo is finished. On this job (if I get it) I will rent a mini-ex with a breaker hammer this time for the concrete work. I figured 2 weeks for the project including the rock fence work.
I have heard some people say that it cost as much to take a pool out as it does to put one in.
Good luck,
Tim