I did one a few years ago about that same size. It had a metal frame around the edge about 3 ft down then a vinyl liner with sand underneath. No problem with drainage once the vinyl and steel was out. Had a sidewalk all the way around and block retaining wall on one end that came out as well. Layed the slabs and block flat in layers and used the gravel and sand from around the pool and what was back filling the retaining wall to fill in the voids. This brought me up to about 2 ft from the top before adding any regular dirt. Customer was in no hurry so we waited a couple weeks and let that get rained on a couple times and settle. Then we cut back the bank where the retaining wall had been to a gentle slope and used the dirt from that cut to fill it the rest of the way up to almost level, compacting about every six inches as we went. Graded off halfway smooth but left a slight dip to hold rainwater rather than let it run off and let that settle over winter about six months. Had experienced some slight settling come spring but honestly not much. Added several loads of aggregate fill to top of that in spring to bring about level and continued to allow to settle. No noticeable settling the rest of that summer. That fall we built up the whole area with about a foot of crusher run. The following spring we built a 32x48 pole barn garage right over top of where the pool was. The building straddles the old pool both ways so all the poles and footers are on virgin ground. We put in 5" of fiberglass reinforced concrete as well as wire mesh for the floor a just to be safe. The building has been up almost 2 years now. I was there a few weeks ago doing some other work and went in to check out the floor and there isn't a single hairline crack anywhere. I was really leery about that job at first but we took our time and didn't cut any corners and it turned out well. That is the only pool fill in I've ever done. I think the biggest thing is just allow it time to settle. I don't care how well it's compacted, there will be at least some noticeable settling. Just allow for it and make sure the customer understands it and it shouldn't be a big deal.
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