Hi Justin
Good luck on your pool! We're in our 3rd season and loving it.
I asked for beach entry when we were designing our pool. My daughter was 2 years old and I thought it would be more "user friendly" for little kids. It would have added about 4-5K to the price of the pool. However when I saw how much of the pool got eaten up by the slope of the beach entry I opted against it. As the pool designer pointed out, it would be great now but when my daughter was 5 (which she is now) she would rather have the added play space versus beach entry. He was totally on target. Now I'm very glad I opted against beach entry. We decided against a diving well for the same reason. We would rather have the play space that comes without having sharp slopes on the floor of the pool.
Our flagstone retaining wall was 12K (trust me, everything costs more here in Washington, DC metropolitan area, it is crazy cost of living). The water feature was around 1K more or less. We have a built in bench on the deep end and a "cozy corner" seating area built into the shallow end and they cost $2500 EACH. Other options were salt water chlorine generator, Jandy RS link controls, integrated 8 foot spa, jumping platform, tumbled bluestone coping, 3M quartz on the plaster, there were a few other options I don't remember including the cleaner thing.
Our pool builder charged based on size, not shape so free form was no more expensive than rectangle. Your area will probably be cheaper to build these options than mine. It's crazy expensive here and you can't DIY very easily as you have to be certified by the county as a pool builder before you can pull a permit to build a pool.
MD Pool Mom