Thanks Ben. Lots of good info under the Kelley Technical bulletins.

Using a concrete mix is good news for much of the patch work. I don't mind "mud" and trowels. Would a sand based thinset work? (NOT the premixed stuff). Or what do you recommend?

I remember seeing a specific caulk tube a while back in an instructional pool video, with the backer rod you mentioned. The caulk was $15 or so a tube I think. I'll look for it and compare with the Kelley docs.

Aside from 9 hours of pressure washing, I've moved the filter/pump, re-plumbed everything and just need to prep/paint, and finish electrical. My goal was to do it all for $1,000 to 1,500. I hope that's still possible.

I'd prefer to leave the chlorinated rubber though it isn't in great shape. Paint sticks to paint. The patches of bare concrete and pitting are what scare me. The cracks I think I can handle. My primary fear is that the paint won't stick to the parts of bare concrete, or the new concrete to the pitted areas. Am I being too paranoid? Will any chlorinated rubber work, or must it be Type A, etc? Home Depot has a $49 chlorinated rubber, but the MSDS mentions acrylic. ??

Maybe I'm wrong, but I don't think the time and money it would take to remove the existing paint and start over with an epoxy is worth it for this house. It's a 16x32, 3-8ft pool in an older/ordinary neighborhood. Plain Jane, concrete box in the ground with a massive Oak next door. My primary reason for the project was to solve a water loss problem. Secondary concern was the appearance. The patching and two coats of paint I hope will solve both. Since I found the 3/4" hole (blocked by paint), I'm pretty sure the 250+ gal loss a day last year (with evaporation) will be resolved!