How long do you plan on owning the house? How long do you plan on living? Do you care about what the pool maintenance will cost your heirs? These are the questions I asked myself when I was trying to decide on plaster vs pebble. I've had both now. Plaster is waaaaaaaay more comfortable.
Does pebble hurt my feet? No. But I don't play volleyball for hours in my pool. Those that do might have something to add about pebble. None of my guests or kids have ever complained about the pebble on their feet. No one's been injured by the pebble.
Is pebble uncomfortable on my bare skin? Yes. So if you might find yourself and your SO sitting around in your pool sans suits, you're not going to like sitting on pebble. When I was trying to decide, my plaster guys happened to have an amazing showroom. They had multiple pools, all with multiple surfaces. I got in up to my knees and walked around on everything they had, and I rubbed all the surfaces with my hands. I decided then that I could live with their mini pebble. Fast forward to the first swim in my pool, and I realized what I had overlooked. Skin on feet and hands is way tougher than just about anywhere else. Especially elbows, knees and tushes. Plaster is more comfortable.
Would I do it differently? No, I'd still buy pebble because I'm more interested in longevity than comfort. Here's how I did the math. If I stay healthy I might make it another 30 years. If I do everything I can to care for my pebble (using TFP methods), I'm hoping it'll last that 30 years. Even 20 years will be OK, as I don't think I'll be swimming all that much for the last 10. And I don't expect my kids will be using the pool much in 20 years. My kids won't likely live here when I'm gone. They'll sell the place. They won't care if worn out pebble will affect the selling price, so it'll be the next owner's problem. If I had gone with plaster, I would most likely have to face another re-plaster. That would have been about $5K now. I expect it'll be $10-20K 10 or 15 years from now. So that might be as much as $25K total in my lifetime for plaster. If the pebble lasts, which was about $9K, I'll save up to $16K. Money I'd rather spend traveling in my old age. If the pebble poops out before I do, I'll lose this gamble.
If money is no object, get the pebble and have it polished smooth. Or replace plaster every 10 years or so. If you'd rather spend "pool money" elsewhere, then calculate the years you might be using the pool (or your heirs), and then do the math: how many times might you have to replace the pool surface times what that might cost with inflation. If this is not your forever house, then get plaster: enjoy the smoothness and the savings.
Don't bother considering home resale value. Depending on where you live, pools don't add much to resale, if anything at all. So it isn't going to matter what your pool surface is, or how much longer it's going to last, neither will affect your selling price...